However 1000 is the maximum I would send my first month unless I had my lead capture system in play.

Buying off market distressed properties will allow you to instantly capture more equity.

I would say two things drove this deal south.  1, lack of due diligence concerning inspecting the whole property - there were issues that were not found that may have been with a more thorough inspection, and 2, too many chefs in the kitchen and none of them actually responsible for how things turned out. 

I have a giant spreadsheet that captures all regular expenses.

So if you are comfortable with the landlord part and want to capture some of that profit (and are reasonably certain that you can do it without overspending), then maybe you want something that you can force some appreciation on.  

Make sure if you do this, you put a place where you capture email addresses.

The towns already have the mechanisms in place to capture revenue from rentals with occupancy/excise taxes and there is the added Cape Cod & islands Water Protection Fund excise tax of 2.75%.Keep in mind that different towns have different registration policies and fees but even the highest registration fees aren’t over a couple hundred dollars per year.