Assuming you have a copy of your documents, there is an easier way.I use Word to convert all our documents into individual PDF's and then use Adobe Acrobat Pro to combine them in one long fillable PDF.

Two or more individuals are combined for a group average score. 15 or less, and we don't rent to them. 16-20, and they pay a double deposit. 21 - 25, and they pay 1.5x deposit. 26-30 pays 1x deposit.

The combination can create a "live in it til I own it" type of atmosphere and closings run 120 days.

Seems like it's probably a fairly saturated market with slim margins, but considering it's a hobby already, might as well combine them? 

I use a combination of excel and a notebook. 

I am looking for some creative ideas or combination of loan types to put me in a position to buy land (maybe owner finance?)

The home loan was based on your combined borrowing power.

Otherwise, renovate the garage into a man cave, while keeping the garage elements to easily convert back with no or minimal cost in the future.

You want to make sure that it's paying itself down not just maintaining the HELOC.Some combination of that and cash should be pretty favorable for you!

Combined rents on the property net roughly $4200/mo after expenses (PM, taxes, ins., etc.)