(The time frame for this was extended due to a natural disaster extension provided by the IRS.

This is the problem with taking payment for the last month when a lease can extend indefinitely.This arrangement is illegal in PA due to a court decision 10+ years ago.

Ultimately I do not want to be over leveraged, stuck paying a high mortgage for extended time, or live in a home that needs work I can’t fund what are your thoughts and recommendations for how I should structure my first purchase?

Essentially, we want an extra room with a bathroom and a small kitchen primarily for our own use and for extended family to use.

lol Our high season really extended into October last year; however, I don't anticipate that to be the case again this year.

Friends, family, extended family. 

Those relationships do not extend to the customer .

I am looking at a constructing a single family that would extend into the floodway (not Floodzone) of a studied stream.

Long story short, the nurse was supposed to extend another 3 months but there was a fight in the street with the neighbors across the street and the section 8 tenant got involved.

One thing I would add is to look for the concentration of nearby extended stay hotels, e.g.