We have it set up where they can upload their proof on a regular basis right in their online tenant portal.

Upon sale, gains are taxed as long-term capital gains, calculated as the sale proceeds minus your adjusted basis (initial investment reduced by any return of capital).

Quote from @David Martoyan:You need to be thinking outside the box on a deal-by-deal basis.

If you are organized enough to forsee hang ups and talk with your GC about potential challenges on a regular basis, two brains are better than one.

What would you say is the average occupancy and daily rate for a 1500 SF 3 bedroom home in good condition around a mile from the beach / pier? 

The $100-$300/month amount is just a generalization - but the point is, on a monthly basis you don't see a huge income per property - and you also have to absorb repair expenses and such as well.   

It is virtually daily that i see purchases or considered purchases that appear to have no path to success.  

The difference between the cost for a specific repair / renovation if you have a crew or need to find someone on a first time basis can be significant. 

Any time you are looking for updates to your build, we have a dedicated email for you to send requests to – we ask for 72 hours to respond because we have many builds, clients, permits, jobs, etc. that we are tracking and working with on a daily basis– and of course we value every relationship.

All in all - owning a place to rent to other people is a business, and business decisions need to be made based on that cold hard facts and not on an emotional basis, unless someone wants to quickly go out of business.