When we bought ours we had to kick out all kinds of problem tenants, but we remodeled them nicely and are very strict on the type of tenants we allow so everyone feels safe and comfortable living there.

If you feel more comfortable having a lawyer review it, that is still a stronger starting point to save money since they are not starting fresh. 

After building up a comfortable portfolio with decent cash flow, I could use the VA Loan to buy a house hack in an area that I like, even if the cash flow isn't great.I would love to hear you guys' thoughts on this and truly appreciate any feedback. 

the thing about automation, you can slowly add what you are comfortable with.

My current income is sufficient enough to cover my living expenses, live comfortably, and put a portion toward savings each month.

Dear [Tenant's Name],RE: External Window Air Conditioning Installation and Removal GuidelinesAs we approach the warmer months, we understand the need for comfort within your living space.

If it is vacant, you feel confident and comfortable with the other contractor after doing your DD AND they have a lower quote, why not give them a go?

As long as your comfortable with your numbers and the sustainability of your cash flow there's nothing wrong with higher equity to get that cash flow.Or the other way with 2 smaller properties like @Peter Mckernan said.That's the beauty of the 1031. 

I was wondering if you're comfortable sharing some insights with me.If so, could you let me know what trends you've noticed in terms of vacancy rates for your unit(s)?

I would do it too if I were in your shoes.