I know they say you get what you pay for but I am impressed with this STR PM, and I use Steesa and Innago. 

- If i Sell , as this was my 1st house and lived in 4 years, do i need to pay capital gain tax ?             

Also, if you are a minority, WRA has the Partnership for Success program, which helps pay for your start up costs.

I’d recommend interviewing a handful of companies, asking for referrals, and making sure the team you choose has a multi-layer review process—so it's not just one person handling your books, but a team with oversight and checks & balances.And totally agree with @Markus Shobe: you get what you pay for!

More than happy to partner up or pay for the deal itself.

I was studying the market and my rent will be just enough to cover the mortgage and HOA fee now I might to pay out of pocket for insurance but don't want to sell it yet because the area is growing and might have good appreciation in the years that follow.

Tenants should pay for that.My lease considered normal to be a few items hung using 1" nails or smaller.

See if you will have to pay for recapture.  

That will increase your material costs for the job and is the contractor paying for the material in their bid or are you paying for it and paying them a labor cost.

If your willing to do so, you can live in the casita and then rent out the main home and have your tenant pay the majority/all of the mortgage (depending on what type of deal you find obviously).