Given your background and experience, you are obviously aware of that being penny-wise is often pound foolish ... so, I'm guessing you are playing the role of instigator here to ensure the other end of the spectrum is considered.

I have stayed in vacation rentals that are primary residences and they must couch surf when it is rented; that isn't what I'm talking about.The recent podcast has my brain chugging about vacation rentals.My husband and I have discussed opening a B&B in retirement, but decided it is too involved and maybe not playing to our strengths.

Obviously their are some variables that come into play but if you have some questions feel free to direct message me as I could answer any questions if you chose to go that route.

Finding a career after the military will also play a huge role on where we decide to invest.

As you know, negotiation/sales plays a major role in every aspect of business.See you around the site!

With that said, I see both pro's and con's of playing in an inflated NY market versus using my current connections in a smaller (less lucrative?)

Part of what you want can be addressed using "mail merge" feature in Gmail/Google Spreadsheet (https://developers.google.com/apps-script/articles/mail_merge).

I think this could play out nicely for you.Rick

I'd rather die doing something, than live playing it "safe" and doing nothing!

Marriage is definitely a team sport, but each player has to realize they do not have to play in an identical way to be a good team.Having a good deal happen can help.