Is there a way that I could submit properties to someone and pay them for doing the comps for me? 

So in addition to what Steven said about track record and due diligence, investors should pay close attention to how the capital is structured.  

I can pull a HELOC on my investment property in KY, pay outright with cash or finance through the installation company.

Hi @Irving Rivera - I think the old saying that "You get what you pay for" holds true in real estate investing too.I think Chicago neighborhoods like Garfield Park are great IF you have the right team and MOST IMPORTANTLY THE RIGHT TEAM COSTS $$$. 

Maybe there are some things that i should pay more attention to, anything I should consider/calculate upfront which for other investments is not necessary?

To add insult to injury, every company I’ve asked for a quote based on the quote I got from the first vendor, wants me to pay another several hundred dollar service fee to come out and look at it themselves.

Can you save more or get it so you are at 20% down and therefore don't have to pay PMI?

65% of your success is the list, not the letter.I totally disagree with Jonathan about saying you will not lowball.You will, and then you look stupid.Unless you are a realtor and can offer listing solutions, I would say you will NOT pay full retail so you don't get all the calls of worthless leads that want full retail.The only reason to do this is if you are a rookie and want practice talking to people.Easier and cheaper practice is to go to craigslist or facebook marketplace and call landlords that are renting and ask them to buy.Your letter is fine, if you find a motivated seller, they will call.

I’ve recently found a part time hustle that pays the same as the full time W-2 for about half the hours and I work when it’s convenient to me.

Now you need to figure out how to find deals and pay for them.