My dilemma is to convert before winter OR save up and do it next fall.

BP is the ultimate real estate investing site around!

Nothing to do with the purchasing of real estate, obviously, but to help yourself out in the beginning and also as a potential alternative means of saving/making some extra money long-term?

All my advice is based off the fact that you manage your own projects and don't hire a GC, as this will save you a big chunk and will tighten your budget.

Gorham Savings Bank and Bangor Savings Bank offer loans in that range, as well as NBT Bank which is relatively new to this area but well established in surrounding markets.

Personally, I find #3 to be the most valuable as it lets me know if my spreadsheet + intuition ultimately matches up with the sale price.  

As long as you have enough savings to be protected in case you just break even or lose a manageable amount of capital, you're good. 

The biggest reason people don't use an agent is because they want to save money.  

Had some cash saved up from working a full-time job in logistics and a part-time job teaching tennis, and bought a fixer-upper for $29,000 with a tenant in place at $700 (sounds like the $30,000 pig, right?)

Whichever market you ultimately choose, make sure you understand in which part of the "real estate cycle" that market is currently in.