@Sam WishIt's going to be hard for many here to provide meaningful feedback as you seem to be framing the issue appropriately. 

If you are able to jump these hurdles, your plan is solid, but I encourage you to spend time here learning and reading.

One concern I'm having is the band of homeless that's taken over the corner a couple feet away, I know they can be transient (my family has been in The City for almost 100 years), could be a deal breaker if Mayor Breed continues encouraging homelessness as previous mayors have done.Originally posted by @Amit M.

Perhaps with a newer PM or a PM that wants extra money under the table, while I don’t think it is likely I do encourage you to ask out of curiosity and experience.

Therefore , I take all measures to avoid it :- Encourage the PM to get me a long-term lease and willing to do price reduction for that .- Make sure PM takes good care of the tenants. - Prefer families w/ kids in desired school districts ( how often will they want to move ?

I commend you on your focus and determination at such a young age and encourage you to continue networking and learning via social media as well as here on Bigger Pockets. 

Thanks for the encouragement.

I really appreciate everyone's reply here, whether it is negative or encouraging - I want to see opinions.To be clear, i wouldn't just be using this money as an investor, I would actually be building a company with the family, and if successful become a partner.

I’ve seen an LOX written to say some versions of the following; 1) This new property has a garage and I need a garage. 2) The new property has more/less sq. ft. and we need more/less space due to x (having a child, downsizing, etc.) 3) The new property is in a different, more desireable school zone (if applicable). 4) The new property is closer to where I work (or go to school, etc.)Although it isn’t always an ideal living situation for some people, I would highly encourage anyone in your situation that is investment-minded to use each of your VA loans back to back for each of you to buy a 4-unit building as the numbers tend to work best on those here in Clarksville and it would make sense, as long as the numbers work, of course, to get as many units as possible with zero out of pocket while you can.

I feel like I’m very blessed and lucky to be in my current situation and that I could be better utilizing my financial situation to build real wealth instead of clawing away at it annually via W2 wage income only (and saving only ~$70k/year).Unfortunately when I model out deals, with today’s cap rate environment, I can’t find anything that generates meaningful levered free cash flow.