I think most people would argue that leverage lets you get into many deals so that 1.) you're spreading your risk, 2.) you have more appreciation over the long-term, and 3.) you have tenants paying down more mortgages over the long-term.  

Expenses: holding costs such as utilities, taxes, insurance, lawn, snowCity fees - permits, potential fines and assessmentsLending fees if anyI would get an attorney involved and write up a partnership agreement that you're both ok with.

I just looked at FEMA maps, and these areas are zone X - low risk.  

I'm curious if most investors here still have a day job and just invest with extra money versus being involved with real estate full time?  

Those considered sophisticated are those that have an understanding of the risks associated with investing.

Obviously, this is all about what I can negotiate though I'm looking for a fair starting point... and also trying to be mindful that I should take care of the investor.I'd either need $260k to buy the property subject-to (but risk the bank calling due-on-sale) or I'd need $757k to buy it outright.  

When investors come to you with a proposal, how do you evaluate the risk?

The VA property appraisal process is much more involved, with more that can go wrong, compared to a conventional loan.

Like you said, I know that involves dealing with a lot of generalities, but it would help me with planning.

In fact, if insurance carriers found out that you are renting, you may run the risk of getting dropped from your policy or having a claim denied - see the AirBNB forum below:https://community.withairbnb.com/t5/forums/v3_1/fo...I am independent insurance agent serving Alabama and I'd be happy to help you navigate this process.