For fulfillment you can do it yourself to save money if you are broke, but ultimately if you want better response rates and focusing your time on value-add, then you will want to outsource fulfillment to a shop that has economies of scale and can offer you great rates.

Having a steady job will allow you to save cash for down payments on properties.

I'm am currently saving up money because I do eventually want to invest in a house and maybe fix it rent it out for cash flow then sale it.

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

Maybe you could get the neighbor to buy 1ft of land from you, that might resolve it easily.  

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.

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.