I currently live in Tennessee and I have a possible opportunity to in move to the state of New York for a two-year work-related contract come the summertime.

Used PSI last year, they did a bad job, the snow wasn't even bad last year and with several attempts asking them to do better within the terms of the contract, they still sucked. 

It is probably worth your time to connect with BOTH @John Warren and myself since we are both managing brokers, but John is more focused on property management and I am more focused on general contracting, but we are both Chicago investors as well.Oak Park and Lawndale are definitely two different markets.

I have been renting out the first home to a family member under no official contract, but i want to establish it as an investment property.

Fortunately, I just call the bank and tell the address of the property I am under contract on, and when I want to close. 

Are you locked in on the contracts with the current set of tenants?

It also might stigmatize the property if you go Under contract and fall out on the MLS multiple times. 

We found two contractors and the bid we received to finish the work were higher than the bid we contracted to complete the entire rehab! 

Here are some key elements to include:Lease Agreements: Ensure your contracts reflect the latest laws, such as notice periods for entry or rules around security deposits.Fair Housing Compliance: Familiarize yourself with federal, state, and local fair housing laws to avoid discriminatory practices.Property Standards: Regularly inspect your properties to ensure they meet safety and habitability standards.Tax Documentation: Keep accurate records to comply with tax reporting requirements.4.

Our first accepted offer was a 320 unit deal that we contracted, put up non-refundable (yeah, I know) earnest money, and thought we had our financing and money in place to do the deal.  2 weeks before closing a major (several million) partner pulled out leaving us short of the funds needed to close.