What criteria do you use to decide whether to keep the current structure on the property or to knock it down and build a new house?

If it were me, someone who is motivated in a buy and hold strategy, I would decide to keep the property which has many benefits such as growing equity, monthly cash flow, HELOC opportunity, tax benefits as a real estate investor (expenses and depreciations on home), and some others.

-Bob decides to re-invest only his gain (because he only pays taxes on the gain) in QOZ on March 15, 2019. (6 months later)-For his 2018 tax return, he will make the appropriate election and pay no taxes on the gain that year.If Bob, holds the investment for 5 years, then 10% of his original gain is permanently excluded from tax.

So I decided to cut down that tree and dispose of it.

Also in terms of multifamily, you need to decide you want to go with the residential mfh (2-4 units) or jump to commercial ones (5+ units).

. - I decided I didn't want to mess with it because Im starting another project with higher potential return.Now, as an example, I look at this one:https://www.zillow.com/homes/63-GRANVUE-DRIVE-BELL...Its on the Auction block, if I picked it up for 2 or 3k, and sold it for 10k to someone else who wants to work with it, essentially a wholesale deal, and didn't spend any money fixing it up, and agreed to max 1k realtor fees if any, I might make some money on it.If you go to our county tax assessor site, and search '63 Granvue', youll see that 1) the total taxes for 2018 are $2981.38, and 2) they are paid by the bank already for 2018 http://www.co.st-clair.il.us/Pages/parcel.aspxWhat I am asking is - if I bought this at auction, and sold it within a couple of months as a property someone else can rehab, how would the property taxes work / what would I end up paying? 

Something clicked and made me remember this site and I decided to join.My background: I’ve been in sales most of my working career and abt 3 years ago I started doing mortgages at a major company and loved it.

They will decide if your proposal matches with the city's intent and decide accordingly.

But since then I have decided not to do the deal because I’m not really getting a great feeling from the property management company and their is an electrical problem they have yet to figure out.

We decided long ago that we won't even consider a SF rental simply because we want to avoid ever having to make a mortgage payment out of our own pocket if possible...That all being said I know there are people out there who prefer SF so it really is just about figuring out what works best for you.