LLCs can provide great asset protection (contrary to what many may say or believe), BUT...big BUT here, it must be set up correctly and maintained correctly. 

Lots of providers, RLI is a good one. 

If he starts asking questions about why I don't want to renew his lease, do I need to provide any answers?

Hello = jumping in on this thread; I'm a longtime rehabber and housing provider in NE Ohio. 

Given your situation and concerns, here's a breakdown of considerations and advice:Pros of Renting Out Current Home and Buying a New Primary Home:Living Condition Upgrade: Moving to a larger, newer home with boutique features can improve your living space.Rental Market: West Town in Chicago generally has a strong rental market, which could provide good rental income from your current home.Portfolio Diversification: Adding another property to your real estate portfolio can enhance diversification and potentially increase long-term wealth through property appreciation and rental income.Cons and Concerns:Interest Rate: The current interest rate of 7% on a new mortgage is high, and there's uncertainty about future rate decreases.

We are interested in someone who can provide a second position loan of on some of these.

They can provide insights into which neighborhoods are safe and have strong rental markets.

@Billy Houston- thanks  1) DSCR might work very  well for you ...if you can  qualify for a standard  conventional 85% ltv  loan - this would provide better  loan terms   2) yes - DSCR is very different than a cash out refinance 3) consider  getting fully pre approved for a standard  conventional loan at a 85% ltv ..this is  crucial  to do if you are looking to buy in a competitive market - thanks and all the best 

There are some very good people on BP who are willing to provide suggestions, recommendations, and insight into various real estate topics. 

I could review the stuff for the day or week and adjust the categories then if needed.I used a single CC for supplies, and a single checking account for all labor. providing the ability to match back expenses without having to check a bunch of different accounts.You could do this with different cards for each project, and a labor bank account for each project.