Does anyone have any tips, cautionary measures, and/or words of wisdom on this approach?

How can I measure the ROI and other factors of a property to manage my risk the best and invest smartly? 

@Joshua Strickland Universal sits in Orlando and there aren't any STR near it (not legal ones anyway), but with Covid the numbers shifted over the last couple of years and we had a lot more domestic travel here from people looking to get out of their homes or states lockdown measures.

Walk a house any house take some measurements call around and get estimates from different contractors.

Cost can be measured in money, effort, time, stress...For that reason I don't think cold calling really is cost effective.

After re-reviewing past income statements and doing my budget forecasting for the year I was thrilled to see I hit 38% expenses against my 2014 Gross Income on one of my rentals.  But after some research on getting a ...

Sometimes we'll even bring a gift card or baked goods just for good measure :-)There are certainly those occasions where tenants are difficult or argumentative, but it's not often.  

Please do not bother to send me points on how to write letters to tenants; mine was very much to a point with all the data, comparison photos, prices....I just think if as a business person himself he does not value my business why should I renew the contract especially now he says he is under duress.If you want to be nice explain  tax and inflation are causing this, so they can vote correctly when parcel tax and other measures appear on ballot.Although you do not need to tell them anything, just provide option and let them decide.

I'm interested in what measure you have taken to get started.

**Relevant information:- Third floor cannot be a permitted separate unit--there is only one entrance/exit stairway (MPLS requires two), and no sprinkler system (which would allow us just one exit)- Third floor electric and gas can be measured separately, but all are under the same bill- By rekeying two doors, there could be completely separate access to the second and third floors- Current second-floor rent is $2000Option 1: End Lease and Rent as a Full UnitThis is the most straightforward option.