I feel that I’m at the precipice of this.

All of the advice listed this full of knowledge and I will definitely try those methods as well.

Renewal options are a better way for both parties to feel good about the agreement.

Feel free to ask more questions and best of luck!

(If you're outside Milwaukee, feel free to chime in too - just wondering if there are unique needs in our area, but general feedback welcome too.)Thanks in advance for any insight!

Also, after reading RPI by Brandon Turner, I'm aware of multiple strategies, but since I've never actually invested or bought a property yet, I feel like I'm overwhelemd by all the options, and find it hard to get started. 

However I feel like we are missing out on tax deductions for the business, since those transactions are not being made from the business’s account.

I hope to gain lots of insight and knowledge from experienced investors in the Bigger Pockets community.

Look at your monthly payment (PITI = Principal,Interest, Taxes, Insurance) + HOA + (other maintenance fees if any) and if this amount is less than what you charge for rent (whether its Long, Mid, or Short Term rentals) and you are happy with the positive cash flow, then yes.Or maybe you're breaking even with the condo but you have  knowledge that the condo will explode in value due to some business/attraction/law/policy that will prop-up the sales price in the near future, then yes.Really, it boils down to what your goals are for this first investment.

I'd suggest you continue on that path and grow your profitable doors until you gain other skills/knowledge in construction and rehab.