Reserve funds should handle a major cap x like a roof, plus money to pay the bills while the work is being done as a tenant likely won’t be paying during this time.

Now the minimum standards your basement has to hit for it to be able to count as assessed sqft not estimated is a height of 7 ft, a point of egress (bilco doors) and a window usually in the rear, It's one of those things where if your going to go through the process of digging out a basement you might as well go for it and dig it deeper then 7 and closer to 8 ft so you actually stand out compared to the competition.Now the other side of this coin which I would suggest is if you're willing to spend 40-50k on a basement dig, consider adding a 3rd story addition if your a 2 story (think master suite, walk in closet, master bath) or an addition off the back and add a roof deck if your a 3 story (either master suite or just additional bedroom).

My husband and are under contract on a great 2 flat with illegal basement unit off of Logan Blvd in a desirable location in Logan Square with a lot of rental demand.

Any other possitive factors  - stable tenant base  - alarm systems  - regular checks on the property  - no pets  - Lead safe certification  - newer roof, plumbing, electric, etc..Anything to balance off the lossesBe prepared that it may end up in a non-standard (surplus lines) market for a couple of years.If you did not have flood coverage before, see if they will continue the current policy if you get Flood coverage and increase the property coverage deductible. 

The roofs were updated in 2021.All units are currently occupied on month-to-month leases, with three tenants paying $1,425 per month and one tenant paying $1,300 for handling lawn care and maintenance.

Hi there, I am running a business with property management, construction and investor focused agents all working under one roof. 

Plumbing, roofs, HVAC, hardscape are expensive.  

After that my contractor will be taking a look at the foundation and roof for me before i place any deposit.

Roofs are $10-15,000 for a typical duplex where I live.  

I have a 3 flat in Lincoln Park, Chicago, IL that I am planning to list for sale in the next 3-6 months.Currently owner occupied in 1 unit (Duplex up, 3 bed 3 bath).The other 2 units (2 bed 1 bath each) are rented.I am wondering if it is more attractive to buyers to leave the 3 bed 3 bath unit vacant when I move out, or should I place a tenant in there and then list for sale?