But rule number 1 and 2 in investing is don’t lose money.

These small conveniences can save you time and money in the long run.For rent collection, you can try Rent.app, which is easy for tenants to use and keeps everything streamlined.

The only thing we can think of is he deals with a lot of international trade and money and maybe it’s OFAC we just get a scripted message every time we talk to someone so we got lawyers involved. 

That's why STR/MTR brings in more money...they're also more work.

Even if you break even, you will lose money every month it sits vacant, when you need repairs, property management, etc.

Would it make more sense to move the money we make from selling to a different property that could potentially increase our cash flow? 

Also, after a year, the mortgage hasn't been paid down by much, especially if it's a 30 year mortgage.The only challenge you may run into is if you purchased it using a low or no money down mortgage option like FHA or VA lending.

It would be a tight budget but I do have money set aside for repairs.

You are bleeding money now, but each year it might actually get worse depending on the financials. 

It took them 3 months to get my money invested and paying monthly.