Can you build an ADU on your current property, then rent it out and just stay in your current house? 

Pushing back will require a skilled attorney with knowledge of HOA law.

I would try to stay within the beltway as you go too far out you will deal with less of a tenant pool. 

Anyone have any knowledge or experience with this?

@Mike HwangThe following general guidelines and things to think about will help you look into joint ventures and get hard money loans for investments in commercial real estate:Securing Hard Money Loans: Flexible Approval Criteria, Local Real Estate Forums, Real Estate Associations, Lender Relationships, Online Research, and Consultation with Experienced Real Estate Agents and BrokersInvestigating Joint Venture Financing: Make Connections and Develop Networks, Acquire knowledge, recognise complementary skills, determine project suitability, draft joint venture agreements, find dependable partners, seek professional advice, and make use of regional real estate groups and networks.Recall that thorough research is essential when evaluating joint venture partners as well as hard money lenders.

@Thomas Yourkiewicz - There is a great deal of information on BP about Toledo to help you understand its national appeal vs other cities, price, cash flow, and ease of entry are a few.My biggest lesson learned in Real Estate in general is - whatever your niche, you will do just fine provided you specialize, create an offering that meets a need in the market, and stay the course when you have hurdles.This holds true if you specialize offering housing to professionals who need high-end temporary housing while assigned to long term projects...medical facility rentals with nursing staff provided...and for every aspect of servicing the investing community (hard money, note buying, appraisals, etc) which gets you out of the landlord role altogether.One sure way to fail is to constantly shift your focus and jump between cities, neighborhoods, or investments. 

I am a health care worker, I have little to no knowledge in real estate, I am here to learn.

Kissimmee is the most competitive STR market in the USA so unless that property can beat the 100 nearest properties near you with regard to design, finishes, amenities, etc I would stay very cautious. 

LL commits to rent unit for certain amount of time and government determines tenant can stay as long as they desire.  

I am looking for  referrals for CPA’s who have an expert knowledge of tax law and work  proactively to help clients leverage the tax system to meet their goals.