Like a lot of the podcast guests say, perseverance and drive really sets apart the successful ones from the failures. 90% of the issues just required a phone call...I have found this to be true as well, sometimes it takes a while to find the right person/office to call but once you get to the right person they are usually able to take down the barrier pretty easily.

How much extra have you been paying on your mortgage each month?

Renting the other units helps to bring in extra income, and gives you experience with managing a property and tenants.  

If the heat is radiators from a boiler, you have to separate the supply piping and return piping for each unit, then you need the extra boilers as well; you might be able to re-gun the oil boiler with something like a Midco Economite to save some money on a boiler, assuming existing boiler is in good condition and not too oversized for the biggest rental unit.One thing to point out is that you will now have multiple burners.

Plus people will pay extra for quirky, older homes in that area.

It can be a mix of the 2 or 3 combined but there is usually one that stands out above the rest as the driving factor.

Even then, I usually wish I hadn't)

They probably won't have a sump pump in there, but if there is one, look extra-carefully for signs of intrusion a good distance from the sump pit.6.

The maintenance is usually lower because they see the property as their own and they tend to keep things up on it.What are your opinions on buy and hold properties verses lease options?  

It has the added benefit of covering literally everything else as well with extra insurance (Auto, Libel, Slander, Primary, Rental, ETC).