One thing we do as a human is speak at the pace of those we speak to or are raised by. 

Most people leave the same photos up all the time.

Using a VA loan for a second property, where I’d move in and rent out my current home.When I made an offer on a fixer-upper (I didn’t win that bid), the loan officer mentioned it might be difficult to convince the underwriter why I’d need another VA loan for a second property in the same area, especially since the new home is almost identical to my current one (same size, age, school district, etc.).

HI Elias,You can always start off by house hacking meaning you live in one UNIT or ROOM and renting out the other vacant units/rooms to offset your monthly mortgage payment.There are several ways to run and make sure you are maximizing your rental income while keeping your living expense as low as possible.

Now I am trying to decide to sell (take the long term cap gains hit) versus a 1031 exchange (never done one) or just relist it. 

But if you use multiple emails as I do for my businesses each Gmail account will have its own google docs space, I found it hard to manage all under one roof.

HI Eric,You can always start off by house hacking meaning you live in one UNIT or ROOM and renting out the other vacant units/rooms to offset your monthly mortgage payment.There are several ways to run and make sure you are maximizing your rental income while keeping your living expense as low as possible.

Leveraging an owner occupied loan locally most of the time will take far less cash. 

Time will tell.I've always been wary of businesses that cater to a limited market.

I agree with wanting the first one to be a "win", I'm just concerned that makes it harder to find something that will cash flow.