In that scenario, you've potentially got 8 doors and used the same amount of funds.

It also makes things cleaner with other potential heirs. 

I'm an RVA native, born and raised and have had experiences that could if shared with you could potentially be a big help to you. 

I work in group home settings for a living and at my previous facility there were two clients per bedroom which would give you potentially 8 in your house while at my current job there is one client per bedroom which would only be 4 clients in your home.

THEN, I plan to purchase the second home using a FHA or conventional loan (3%-5% down), for which I will likely pay the monthly cost out-of-pocket, maybe with some rental income support if it is a duplex.My concern is, I do not want to spend my savings or weigh down my debt-to-income ratio so much so that I cannot qualify for and pay the down payment and closing for the lending on the second home.Questions: - With the first home being multi-family, 75% of the rental income (or potential rental income initially) will relatively either maintain or boost my debt-to-income ratio from lenders' perspectives, right? 

Strong Potential for Long-Term Capital AppreciationGermany's real estate market has demonstrated a strong track record of capital appreciation.

Indy is a strong market with a great mix of cash flow and appreciation potential, plus it’s very landlord-friendly.

We are always look to help investors and potentially partner on some flips.Wow small world.

Your VA loan will be crucial to your real estate investing growth, especially since it affords you the potential opportunity to own more than one property, depending on your overall allotment.For active military personnel, that conundrum of where to invest and where you will end up is always part of the issue that sometimes causes analysis paralysis so it's great you have one in VA Beach already.

It can provide a very misleading valuation.Your appreciation numbers reflect just below 4% a year (I used 8 year hold) on both properties which is below national average for this period and below what neighborhoodscout depicts for Chicago 10 year average. https://www.neighborhoodscout.com/il/chicago/real-estateLooking at this from the outside, I am missing a lot of details such as your interest rate, is there a prop tax benefit for long holds (by the way look up prop 13 for CA at some point as it may play a role in your decision to purchase once you relocate to San Diego), the neighborhood, appreciation potential going forward, any emotional attachment, etc.