My maintenance is usually less then 1k per year., We replace the roof, and HVAC if 10 years or older.

And then they will accept a % of list price. 

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

Goal would be to acquire 20 rentals by the age of retirement, with some already starting to be paid off.I am in the same boat as you, and I focus on safe appreciation all day (small cash flow for safety and then focused on markets on that appreciate). 

You may need to replace insulation, sheetrock, or even framing material.The only way I would touch it is to have a contractor give me an estimate for renovation, then lower the price far enough to handle that renovation.

Further context, I have zero debt, high 700s credit score, one other investment property here locally. 175k in cash available, looking to do DSCR loans or cash and then refinance.Peoria, Illinois- Great need for lower income housing, market appears to have many options.Lawton, Oklahoma- Looking only at extremely cheap properties, as it seems it’s not terribly hard to find renters.

Ok, then know when in over your head and tap-out! 

I also know I can look at ways of borrowing against that equity (HELOC for example) but I also just feel like if I take debt on that property the cashflow goes down, and then if the association also takes the loan it goes down more, and at that point I don't know why it would be a better option than selling before August. 

When an investor gets over 4-5 in a market then we normally talk about diversifying into a different market. 

@Trevor Halama Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Why is Property Class so important for investors to understand and apply in their investing strategies?