You are also $150k in debt, not $100k.

It it is debt free, that’s another story.  

WHEREAS, pursuant to said Declaration, there is claimed to be due and owing as of the date of this Notice by Jacob Szyperski, as unit owner, to Prairie Bend Association the principal amount of Two Thousand Seven Hundred Thirty-seven Dollars and No/100 ($2,737.00) for condominium assessments, interest and past due attorney fees through March, 2019; and no action being now pending at law or otherwise to recover said debt or any part thereof, and; WHEREAS, pursuant to said Declaration, and the statute in such case made and provided, said debt creates a lien upon said premises in favor of Prairie Bend Association.

I am at a turning-point in my life where i'm still living at home so my expenses are minimal, my credit score is at 800+, my salary is in the 105-110k range (still work at my day job), and I have an extremely low debt to income ratio.

So if your credit low because of high debt that could make conventional hard for you.

Software-wise, you can combine accounting software like Quickbooks and Some tenant management software but you as you say Appfolio is manual entry but some modern software you won't have to.The important point is that you should find the right fit for your needs.

My debt to income ration is like 0.2 (monthly expenses are around $2500/month, and income is around $11,000/month.

Do people see an opportunity to separate the (seeming) unsecured debt from the secured debt?

The best example in my family is my dad offered to guaranty some of his brothers gambling debts to some loan sharks.

I'm not saying that the combination of the two doesn't exist.