For example, if the negotiated TI allowance is $20 per square foot, and the leased space is 1,000 square feet, the total TI allowance would be:TI Allowance = $20/sq ft \times 1,000 sq ft = $20,000Lease Term Consideration:Longer lease terms (such as 5 years or more) can sometimes result in a higher TI allowance because it provides the landlord with stability and longer-term rental income.Special Considerations:In some cases, TI allowances may be structured differently, such as a lump sum payment upfront or spread out over the lease term.

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. 

I’ve heard about ‘gap funding’ for fix & flips to cover down/closing/holding costs in addition to the hard money loan for most of the purchase price & rehab, but how realistic is it to secure that type of funding?

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

Here’s a list of good HELOC providers, in no order.

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.