I've read the previous posts that warn about purchasing townhomes without HOA because you can't always agree with the other owners about fixing the roof and such, but since I will be purchasing all 4 units does that negate these negatives?

The longer you don't pay, the more leans are added.That lean is negated when you have a contract or written directions.It's Your money.

You're not saying this property has negative cash flow, are you?

The rent covers the mortgage, insurance, and HOA, but after paying for property management fees I am losing ~$200 per month, and have little for CapEx, vacancy, and repairs, although it is newly remodeled.Based on my research I know that it is not smart to rely on property value appreciation to justify the negative cash flow, so I have researched ways to try to improve my cash flow:Increasing rent is not an optionProperty management is necessary as I live out of the countryRefinancing doesn't seem very advantageous, my mortgage is a 30 yr fixed rate at 4.375% and the rates in Denver only look slightly below that for attached homesRecasting the mortgage seems like a decent optionUsing this calculator it looks like I could go from Principal and Interest of $1,541.79 down to $1,317.05, for a monthly reduction of $224.74, achieving a slight cash flow positive, if I invest $40,000.

Negatives are taxes are high and increase for a "windy" city, tenant laws strongly favor tenants and most buildings are over 100 years old.

It also doesn't help that until you have enough units in an area, you are inevitably going to deal with various negative variances (e.g. the tenant who seemed perfect ending up being a nightmare tenant).

At first I was so negative about it .

So I would welcome feedback positive or negative on my thinking.  

It may work as a complementary strategy in which I can slowly improve my primary residence, buying slightly larger each time and renting the properties I move out of, but my concern is that if I'm intentionally selecting nicer houses for myself, will I leave a trail of negative cash flow behind me?

An individual on my team has a multi family in contract for himself just walking distance from beach that will be negative for a couple years until it turns positive but its a great long term investment for him.Good luck!