I occasionally would get extremely motivated about investing in real estate, but would often be shot down by others or my own limiting thoughts.

We do not sell real estate, but occasionally we hear from a homeowner client who is interested in selling. 

I have family and friends in both cities, so I'm in the area occasionally and would like to be able to tour properties before buying out of state.

Due to the properties we target, construction, and our process for selecting properties, our average maintenance cost is between $300 and $400 per year, plus an occasional water heater or AC compressor replacement.

And occasionally, I am wrong about a person.

Occasionally an issue will arise (like during a recent refinancing or changing insurance companies), but the City has been great about providing a letter that resolves the issue.  

We occasionally have longer term people stay in the winter, but even when we don't, we still have plenty of rentals.

So at what point is the cost of a tenant turn < occasional late rent?

@Tina Rubin as an occasional lender myself, I think the second option (new deal/property) sounds a little cleaner and more of the traditional lending scenario - if I’m understanding you correctly.Just make sure you have a good understanding of the higher rate you’ll be paying to the HML and make sure you can still make your numbers work with that higher payment amount.A hard money lender’s main concerns will be the value of the collateral relative to the loan amount (LTV), and whether your estimate of the project cost is accurate.The HML will definitely want you to bring a substantial amount to the table as a down payment to keep their LTV low (65-70% is common), so if you need to refi your current property to get those funds then that might be something you’ll need to look into.If it was me I’d probably stick with a traditional fixed loan on the first property and start out with a private/hard money loan on the second, until it’s rehabbed and stabilized, and then refi out with another bank loan.

That said I do mostly wholesale and just pick up the occasional rental.