I am currently self managing 8 units in the Chicago SW side predominantly in the Lawndale and Oak Park area a mix of FM and section 8 tenants.

If you have a self directed account and invest pre-tax money into illiquid assets like syndication or mortgage notes they will come in at a value of less than the principal.

If a property needs too much work upfront, it may not be the best first investment.4.Factor in property management costs—even if you self-manage.

I have several opportunities to snag up a self storage complex and a 18 unit apartment complex on creative financing .

It’s been stressing me out as I self manage this and my other property where it’s affecting my moods and I don’t like it and something has to change.

The market between the 2 locations & resident class (Especially if you plan to self mange or find a PM company), Your future goals and the costs associated with moving and transferring to a new hospital. 

For house flipping, consider an LLC taxed as an S-Corp to reduce self-employment taxes by taking a reasonable salary and the rest as distributions.

I self manage, have a cleaner but I also sometimes turn the unit myself.

The loan is with you, not with your tenant, so none of that means anything to them - in fact because you live in one unit and it's under 4, if you were self-managing you don't even have to abide by fair housing laws (at least on the federal level). 

Although in the last couple deals most have come out as 506C deals where only accredited investors are allowed, there are still 506B syndications where you can be a sophisticated investor (self proclaimed) so you don't have to be accredited.