I thought 1 per year was enough to push me out of my comfort zone, but also not too much to overextend my finances. 

There are companies out there who handle the entire process for you from top to bottom so it can be a very safe, comfortable investment that's seamless for you.Feel free to reach out if you have any questions.

Ultimately, it depends on how quickly you want to act and your comfort with leverage.

This makes it harder for a buyer to evaluate and feel comfortable paying market price for the property. 4.

I'd feel more comfortable with 50/50, so the next big chunk goes to RE. 

You’ll want to make sure the rental income comfortably covers the new mortgage, taxes, insurance, and any maintenance costs.

Most agency lenders, Fannie/Freddie have been asking for 65%, knowing that there was problems on the horizon.You need to ask yourself where do you feel comfortable with debt levelsGino

Its a local business, not a national service which gives me more comfort as I'm not a fan of "home warranty."

Are there any lenders that anyone is aware of that would feel comfortable lending about 325k for a 5 unit property?

There are so many rentals in the area, probably on shared wells, so those people have either decided the STR use is okay or they are comfortable risking it.My intuition is that any actual disagreement over water usage could be handled with the other owner; but the risk would be if the other owner just doesn't like the STR and wants to use the well agreement as a reason to demand it be shut down.Any advice would be greatly appreciated!