It all depends on the particular deal.

In 2019, my wife and I started listening to podcasts, and in particular Bigger Pockets.

Since that matches the model on the deal you already did successfully, I thought it might be better to aim in that direction again.Make sure to run the numbers on any long term holds and particularly pay attention to debt service coverage ratio (DSCR) which is the yearly net income from the property divided by the yearly mortgage payments.

I am hiring a property management since I have no experience dealing with this issues, specifically with this particular tenant who is also two weeks late on his rent.

We real estate accountants can help you minimize taxes, but we won't tell you to buy (or not buy) a particular property out of tax consideration.

You may wish to confirm that the new 401k provider has experience with the particular investments in which you intend to invest your retirement funds as you very likely will have questions in terms of the mechanics (e.g. how do you invest in real estate, etc.).3.

.), which does not make financial sense in this particular case and won’t offer a return in a foreseeable future.

This particular house had a very nice big detachable garage perfect for such a thing.What was the outcome?

I'd be curious to hear some expert opinions on this particular property.

the house has been encroaching the building line (house was built) 20 years ago or more,most title companies in Chicagoland will insure over the encroachment for the Owner's Policy at no cost to Seller/Buyers.HOWEVER, violations of the building lines on the side of the lot might be different particularly if the house is ALSO  encroaching over a drainage or utility easement.You don't tell us the number of feet of the setback on the side of the house and if house also encroaches an easement.Perhaps you could even attach a copy of the Survey, assuming you learned of the encroachment from a Survey.Good luck.