Don't depend on Aircover.Homeowners policy will not protect you if your renting as a STR.You need the correct STR policy to protect your property.

For multifamily or commercial, the rental rate impacts the value of the property. 

For full time management rates can range from 20-30% of gross revenue depending on the level of services provided.

Depending on how the water is getting in, there may be cheaper methods for sealing the basement walls from inside.Keep shopping until you find someone trustworthy with solutions.I would also consider going after the first contractor because they robbed you.

Maintenance and potential repairs will also require a long-term financial plan and setting aside a contingency fund for such expenses.The steady cash flow, appreciation over time, and tax benefits can make a meaningful difference to your wealth in the long term, especially with the principal paydown on the mortgage.However, if managing the property from a distance feels too burdensome, or if you’d prefer the certainty and flexibility that comes with having less debt (especially given the high mortgage rates), selling and using the $100,000 in equity to reduce your loan for your next home may be the smarter move.

And it's very pertinent to today's environment because it doesn't look like interest rates will be coming down much, if at all this year.

.- We also negotiate a reasonable completion date, depending on the Scope Of Work (SOW). --- Who gets all the phone calls and wastes time calming a tenant down because the owner's contractor doesn't show up as scheduled after they took time off from work or a 3 day job takes 3 weeks?

@Mike Levene cost to build per square foot is $200-$300 depending on finishes.So, you can start with that.

It also depends on how you hold your properties; LLC, S Corp etc... as to what the agent will recommend.

Here in Chicago, you should expect a range from $200-$275/SF, depending on the location, experience, labor, and material finish level.Are you in a position where you already own some land, or what is your current situation?