Any guidance would be most appreciated, so we can be better prepared for our tax returns next year.Thanks so much for your time !

Photos of the tree show it has been dead for some time, not hard to tell.the tree fell from the neighbors yard through the fence.

in my opinion it is a particularly tough time to get into wholesaling. 

.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

Anyone have some good tips for wholesaling around a full time job?

For the time being, might as well get a mortgage in one person's name.Best of luck.

If you can't or don't want to now might be a good time to unload the properties.I will say overall I think that "nobody will care more about your property than you" tends to be much more true than false. 

I have a guy who has been here since July, but I renew his short term stay for two weeks at a time, every two weeks.

Might be time to look off-market.

If you are setting aside funds for capex, taxes, insurance, or other expenses that don't occur monthly, transfer those funds to Savings each month and hold them there until it's time to spend them.