I'd rather not ask my agent to continuously make offers with a 1 in 20 success ratio (or lower). 

Those are usually lower-risk people.You also said he has "significant savings" so maybe he can pay a triple deposit (if your state allows) or the first few months in advance.

The second recommendation would be to do a house flip with a special and your able to move there and be a "house hacker" and take advantage of the lower down payment.The only other way away from home is to buy an apartment complex that had a minimum of 30 units so that project could afford property management company from that local area, they need to be experienced and understand what you expect in reporting and current operation with phone talking. 

My now wife (then girlfriend of only one year) jumped right in with me and we closed off a back area that collapsed, removed that from the structure, closed off the upstairs, and made the lower livable.

I believe your depreciable basis when converting to a rental is the Lower of, your purchase price plus major improvements OR current value.

so I am assuming that the capital gain is lower than the ordinary income?

The results would be a far more energy efficient and comfortable building with lower operating costs.  

I'm looking to get into a market with a smaller barrier for entry, thinking about the midwest so I loved hearing about your first deal.

If you are more interested in cashing out, you'd be better off waiting for an offer to come in, maybe lower your list price.

I'm thinking with the BRRR strategy i can buy it at lower enough price where it would make sense to use the VA loan to roll the rehab with it.