The front yard imo now looks terrible and now kind of regret removing those shrubs because it also served as a privacy wall, which I like.I thought about a fence, but now against the idea based on cost, surrounding area, and comparable. 

If you think that you can live in the place and save expenses compared to renting something equivalent then it could be worth it.

If there is a calculator on here that allows me to run numbers for updating an existing property and comparing options, I'd like to hear about it.

You’ll never catch a break or receive an accommodation from someone you don’t know compared to someone you do.

I would just try it and compare.

You might even get a better return over time, i.e. selling two condos compared to one duplex.

The 1031 can help you with both of those by letting you buy more stable real estate and save a bunch in interest charges with a new loan.The problem people have is when they compare only the acquisition price of the real estate with a 1031 exchange. 

Quick looks on realtor or Zillow only show a few houses and they seem very pricey compared to tentative rents.

@Bob OkenwaBob is correct.Especially if you plan on making this a career... mortgage fraud will crush your dreams.A lender calling a loan due in full when they find out you don't occupy a residence you said you would, or when they see your rental posted when you said it was a primary or secondary home is minor compared to mortgage fraud.I once worked for a mortgage lender who has a friend who was convicted of mortgage fraud.

Attached is an estimate from a local general contractor and I'm just curious how this sizes up compared to other estimates you've all seen - and if we'd be better off managing the project on our own and sub contracting specific parts out.