I would set a year built filter with your other criteria and see what it returns...remove the filter and see if the properties showing are something you can be comfortable with.It's more important to focus on the location and configuration of the property and opportunity for value add than focusing on year built.That said, older properties (if not updated) will always require more work to get stable due to inherent issues associated with the building style and materials...stone foundation, slate roof, balloon framing, ungrounded or unsafe electric, and possible abatement of hazardous materials...

If you don’t feel comfortable cold calling, you would have to hire that out.

If I was in your shoes, I would definitely house hack and use as little money down as possible.

If it were me in your shoes, here is how I would proceed: 1.

Therefore we spent the next 6 months furnishing the unit to make it a comfortable, pet-friendly AirBnB unit.

It all depends on your comfort level though.

Don’t just go with one person’s recommendation, it’s an extremely personal choice and where you end up should be where you feel the most comfortable and that you will have the best chance of success there.

I am not sure if I owned a mill if I would really feel comfortable putting a residential tree through my saw. 

We have a gas furnace, but in the winter we find a good electric tower fan space heater and the rigs electric fireplace keep us more than comfortable.

Either selling the properties and using the profits to buy larger properties or just using my personal cash to buy bigger and bigger properties as I get more comfortable.