You may benefit by attending the local Tidewater Real Estate Investors Group meetings and networking to partner with an agent who will work with you when you need information. 

There are plenty reaping the benefits of Short Term Rental Investing, some cities and states it can be more seasonal so throughout the course of the year you may tend to only breakeven.

Recent events have pressed more of a NEED than a WANT- looking to get my brother-in-law into a flip or BRRRR-type property for a few reasons: 1) Get a young single father an alternative living arrangement to current situation 2) Allow him to pay down debt 3) Get him interested in real estate investing for lifelong financial benefit.

In the meantime, I would like to amend my loan type to a more conventional loan so that I can purchase a home in Virginia using my VA benefit.

My target is one new property a year for the next few years as I gain experience in managing renovations and tenants.

Even though I shouldn't give advice I told him about the 1031 Exchange and how he can avoid Capital gains when he sells the properties, which excited him because he wants to get a nicer home with land so he can do farming once he's done with work. 

I think for the time being, I’ll focus on out of state to gain some experience.

I liked what Brandon Turner has said about how your first deal should be more about gaining experience than making money. 

I’ve retained the property as my primary residence for two years to avoid the capItal gains tax and am getting ready to list.

I think I'd like to have all my money back so I can get into another property, while my tenants pay down principal... and I'm budgeting for capex, maint/repair, vacancy, insurance, taxes, and management... but is the benefit of having nothing in the deal worth having almost no true cash flow?