I intend on sending the tenant a bill for the exact repair cost as "additional rent" (per the lease) instead of evicting in the winter and deducting from the security deposit.

@Katie Lyon Because our weather is more temperate over the winter months, we have much more consistency in demand across all times of the year, so typically the market stays fairly consistent through all seasons.

You are walking into a potential situation that can break your heart, break your bank account, or break your will to ever try this again...Maybe if your lucky, all 3https://phillysheriff.com/property-listing/ Thank you for the information!

It's the middle of the winter in Chicago.

I have no particular area that I'd like to start with or focus on, but probably prefer somewhere in the south of the US due to my strong aversion of winter.

What about having to break even, or even feed the property every month $200 for those same 36 months, but at sale, could net a $75K-$100K profit?

Investment Info:

Single-family residence wholesale investment.

Purchase price: $255,000

Cash invested: $100

Sale price: $260,000

3 /1 894 sqft

What made you interested in investing in t...

Investment Info:

Single-family residence wholesale investment.

Purchase price: $255,000

Cash invested: $100

Sale price: $260,000

How did you find this deal and how did you negotiate it?
...

We have had a pipe burst during the cold winter months, the roof needed to be replaced (thankfully covered by our insurance), and some issues with electrical, which hasn't been majorly updated since it was built in 1973. 

I took quite a break from buying properties and now on the hunt again.