Any questions you specifically ask?

A title report is crucial and will specifically display any contractor liens, easements, and other miscellaneous items. 

I'm wondering if I am paying a lot more (or maybe even less) than what most CPA's charge for them to file my personal Fed/State taxes & the 1 investment property I have thats not under LLC.No need to share specific numbers if your not comfortable but anything helps!

So, let me be specific on the scenario. 

Can I deduct my moving expenses on next year's tax?

It is so fun to see their faces when they see the cash flow, tax deductions, ROI, Appreciation, that is possible from one property. 

hard to give useful advice without specifics...

Hi Jason,Here's a few things I'd be mindful of:Separate Personal and Business Finances - get an EIN, open business bank account and use it exclusively for businessMaintain Documentation - keep records of all business transactions and contractsComply with Legal Formalities and Tax Regulation - adhere to all state specific regulationsIn terms of the STR and LTR, it's generally recommended to put them under an LLC by transferring ownership or quitclaiming.

There is a big distinction on the variety of restrictions you need to be aware of with ADUs in Chicago specifically.

Specific to payments, try to push for net 30 payment schedules for your GC.