. - Inefficiency with payouts and administration will be compounded as the FAIR Plan has zero experience with a major pay out and lack infrastructure of assessors and technology to distribute the funds they don’t have.

North side Chicago I have never even had to give a tenant a late fee and none of the tenants I have placed for clients have ever given them issues either, properly picked people pay like clockwork on autopay.

Is it better to keep adding equity by doing work on the houses while I'm renting them then refinance to recover the initial down-payment to reinvest into another property or to pay down the heloc?

Despite paying fees, doing a deal and making some profit is better than sitting on the sidelines. 

One question that you may not want to post here for legal reasons, is how much are you paying your PMC?

We can be flexible when we pay them back.

Who would be responsible for paying this?

Contractors, unless you have a working relationship with them, normally do not want you bouncing ideas off them.Understand what their hourly rate is, have a discussion with them that you are okay with paying them an hourly rate if they walk the property with you and provide you a scope of work along with an explanation of what you can/can't get away with in regards to improvements.ask them if you go with them, if they can credit you the amount that you paid.Once you develop a working relationship with a few contractors, you can bounce ideas off them and expect quality responses.I do not invest in New York.Best of luck. 

I welcome any feedback the online community may have; I am sure several of you once has the same uncertainty in your mind.

If so, adding amenities that your ideal guest will find valuable = they'll pay more for it.