TorchtheFlyingTiger

Schwab, Fidelity, Vanguard or even Robinhood (although I'll take heat for this). Read JL Collins' Simple Path to Wealth and if it makes sense manage it yourself. If you think you need help at least you have a baseline of knowledge to work from when vetting an advisor or picking a roboadvisor.

I played around awhile back with the free versions or trials a few of these tools. I havent pulled the trigger on a subscription yet. I'm still need to find the best one to meet my needs (tax optimized withdrawal strategy and Roth conversions). This guy reviews Boldin and several others you might want to try 5 Best Retirement Calculators Rob Berger
Reading up on boggleheads, reddit etc, users that tried more than one typically observed they give different results and recommendations due to different default assumptions.
Best tool is going to be dependent on what you are looking for it to do and what you are willing to spend.

You may not want to burst her bubble. Best for her to have more situational awareness and head on swivel in future anyway. Besides, probably feeds her self esteem to believe she was chosen as a target amongst all the other women shoppers.

Lump sum right back into the market. Dont fool yourself, converting to cash and sitting on sideline is market timing not true DCA.
I would stick to index funds for vast majority of portfolio and if taking any higher risk/reward do it in tax advantaged where you dont worry about tax consequences of trades.
I dont like dividend plays but if you must, avoid holding in taxable where they will suffer tax drag. No need to generate extra taxable dividend income you dont need.
If you are already competent self managing, 1% for an advisor is more than I'd want to spend. I'd try to find a fee only advisor to QC your plan occasionally and perhaps focus on tax optimized allocation, conversion and withdrawal strategies. You probably get more benefit from good tax professional in short term.
Diversification into other asset classes is probably good idea.
As for building out commercial real estate and active trading, be sure to weigh the value of your time. Even if you enjoy it now, it might be an unnecessary mental burden in a market downturn. Your time is likely better spent in your field of expertise.

More reason to wait. You'd be unnecessarily accruing an additional 8 months of higher interest rate on existing equity loan balance. It might make more sense to keep the lower rate and borrow the $15k when needed on a separate HELOC or personal loan, especially if the existing loan is high balance.

Eaux douce!

No, cash contributions only. You'd have to sell the shares first.

Waiting much longer is going to erode his recruiting at either school. He's going to take blame either way when OM inevitably loses in playoff. Everyone knows his days at OM are numbered unless they sign the massive extension now.

150 miles would meet my need for local driving. The family car is what we use for road trips anyway. If price is right I'd consider it.

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My property taxes have pretty much tripled in the 5 to 10 year with that last 5 years

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How? Is it homesteaded? Honestly wondering because I think I understand how it works but maybe not. Haven't been here long enough to experience it myself. I have family that want to move here but see these anecdotal bits online that make them fear their taxes would soar which doesn't make sense to me. What am I missing? Are actual primary home property taxes for long time residents really sky rocketing a despite level millage rates and SOH protections?

Not exactly your question but would you have enough remaining eligibility to cover 25% of next purchase? From what I'm reading that's all you may need for another VA loan rather than the entire purchase price.

The low rate assumption has a value for buyer but they still need to come up w cash to buy you out of your equity position or get a second mortgage which I'd assume is higher rate than a first. May be a niche buyer you're looking for. Is it listed on sites for assumable loans where such buyers are likely shopping? ETA: not showing up on ROAM or ASSUMABLE