At least one of us should be able to continue working remotely (how do others get health insurance without working a normal job?)

Also, but based on conversations with my CPA, it seems that classifying the property as investment rather than vacation will afford you an increased depreciation opportunity. 

I'm wondering, however, if that's my best first move, or if it makes more sense to keep renting and spend my $40K savings on a deposit for a triplex or quad in a place like Cincinnati where it's much more affordable and up-and-coming? 

These tips can also be used to achieve success in other areas of your life such as health, relationships, etc.1  Positive Mental AttitudeThe only thing in life you have control over is your mind.

But I’m right there with you - interviewing banks and looking for the downpayment terms I can afford but in Burlington, VT.  

There are many affordable investment opportunities in high yield private commercial and residential properties.

If you can afford the tenant turn and the vacant period to lease I would highly consider letting them go as well when this term is up. 

I wouldn't say he's evil, but he's definitely not nice.On the other hand, his monthly net income is about $45,000 so he can afford to pay a judgment. :)

You can make money flipping high end properties, but not so much as a landlord right now.If you want a home,  buy a good building in a decent area, buy as much as you can afford and forget about the price. 

My vision is larger than my fund, and revolves around ensuring that those who live in marginalized communities have access to the social determinents of health (education, economic opportunity, healthcare, and homes) and are able to get themselves on a pathway to generational wealth through home ownership.