Buying an existing place that needs upgrading might be more sensible but it will still cost a lot of dough.Plus the purchase of the catamaran.

However, I have a few concerns:Pros:Living condition: 1400 sqft → 1700 sqft with some boutique featuresThe rental market seems good in this area.Another property is added to my existing real estate portfolio, which currently includes two other properties.Cons:Interest rate: 7% - No guarantee of decreasing the rate, which means there might be no opportunity for refinancing in the future.The current home is too new to be rented out.People often say not to buy property in Chicago due to high taxes and low appreciation.There’s no necessity of moving since I have a decent primary home.Any professional advice would be helpful. 

This policy will provide additional coverage above what your existing policy covers.

To find a house where the seller is willing to sell it to you Sub2 the existing loan you need to do quite a bit of marketing.

In what state such regulation or law exists?

This has not occurred and as such I will now have second thoughts before doing any further expensive upgrades for an existing tenant.

We just get an appraisal done for the rate/term refi and if there is extra cash there we modify our existing loan for what ever the max LTV is for the take out loan.

Lake County is coming down in price with interest rates rising - especially existing builds (not new builds).

It seems like you have a fantastic chance to maximize the space in your existing house so that you can earn rental revenue.

@Guillermo Kennedy, it's certainly possible to use the existing LLC as a joint venture entity; the legally binding agreement here would be amending the existing operating agreement and updating the current cap table to reflect the new members of the joint venture.