Additionally, only my aunt's third appears to benefit from the 250k capital gains exemption.The house has appreciated approximately 300k in the last 16 years. 

I'm self managing the SFR for now to gain first-hand experience.

Avoid short term capital gains?

Hate to sell in a couple years and eat up all those cash flow gains just in commissions and closing costs.

So, I'm interested in learning more about purchasing rental properties.In my quest I can provide hard work and construction skills, especially in pool related area, in exchange to gain experience or potentially work a few deals with you all.It is a pleasure to be on here, and to eventually meet with you all. 

Your background in property management is incredibly useful -- the experience you're gaining is as important as the capital you're raising.

Is there a way to calculate or do I just need to gain experience doing it?

Assuming this was their personal residence and All cap gain is exempt under section 121, and was never rented (no depreciation recapture.)....1) return of basis-no tax2) cap gain-cap gain tax if not exempt3) interest-taxed as his ordinary income tax rate (no ss/med)

Can I pay capital gain on this $ 500 k or I still have to pay regular income tax on it?

I'm a big believer in direct bookings but you'll need to utilize the existing marketplaces first to gain traction then invest in your own site.