Why is the roof ok to do while they’re in there still? 

The learning curve can be steep, but it’s also the most exciting part, especially if you’ve got someone who’s been through it and can help you make sense of the chaos.If you’re thinking about starting small, maybe a single-family rental just to dip your toes, that could be a great intro.

In bankruptcy, he could get out of paying you but that comes with a steep cost for him. 

The con is obviously the cost because in addition to waiting a long time for permit, it requires serious structural changes + roofing, etc. 

Of course capex does come into play, but I have a lot of factors on my side including most major components of the property have been replaced already, including roof replaced 2 years ago, water heater replaced 3 years ago, full house was just repiped, septic system is 5 years old, HVAC system replaced in last 7 years, i do not cover appliances with warranty in my rentals, and the tenant I placed in the property is a single dude who works 60 hours a week and just needs a place to sleep.

Roof?

 @Nathan Gesner Funny you should say that as that is what we did yesterday ..we actually lowered it to $1685 and it looks like we have a renter  hopefully  ( fingers crossed ).Income verified , credit score etc It’s a bit low for me but we can get the mortgage paid, the heloc payments and the roof payments and still put some cash flow in  reserves each month as we will pencil out a bit.

2/3 of the units are singles/studios, so generally higher turnover, causing higher fees for clean outs and lease ups, etc, etcRecently had to get a "fire rated" door to the roof replaced from some city inspection, the first  bids were $3800-$4500, but with the right contractors and a little of my own time and motivation, i got the job done for less than $1500 and 12 hours of my time, and it had 2x the fire rating than the city required.

You’ll reverse engineer top-performing properties and get title & description recommendations, discover rare amenities in your market, & utilize competitor’s reviews to convert more guests.My expertise is in increasing visibility in search engines (and lead generation for law firms, roofing companies, etc) and not the AirBNB/VRBO algorithms.

Your mechanicals and capital expenditures are a lot more important and more expensive to fix than a pretty kitchen. its better to live in outdated kitchen and have a well kept home with updated mechanicals/roof/hvac than one that looks pretty but will start to crumble5.