I’m not sure he has enough appreciation to sell right now and I’m trying to help him decide on sell / MTR / LTR / STR.

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

Now, the next day on 2/25/25 the tenant is requesting that we give them a 25% reduction in the rent for the month, sighting that 30% of the month they have been left without heat.

Now they continually ghost me. 

Quote from @Peter Tverdov: Think at least for the text standpoint it is challenging in this market now where I know personally 3 people that have been in lawsuits with one ringing in at $500,000 for cold text messages to people that did not want to be marketed to, so to @Jonathan Greene point on that for sure.I think that cold calling is a true skill that really no one (or 1%) will end up doing, and I 100% agree that VAs do not do it right..

I have a great one in Kansas City for over 15 years that I've used multiple times (only auto loans however), but hoping to branch out locally as I begin my investor journey in Arizona. 

Keep in mind sales are way down right now.

Paperless documents are very common now.

Now you have to scale.

Some of our owners have accidentally thought they were handing a situation "right", and because Chicago is a very tenant friendly city, the laws tend to lean in their favor, and it can cost you a lot if you are simply just not up to date on what is proper protocol (for example, what to say, what not to say, what to have in writing, and what not to put in writing, etc)... can be worth the management fees.