So ultimately we decided to suck it up and not take on the additional equity, which ultimately required us to take more time on completing the needed rehab, however in hindsight it was a good decision, because even just among our own family there's been lots of dispute on what we want for the business plan and personal STR useage....

Real estate investing has been a passion of mine for time with my mother also having invested early on where I likely have gotten the love and desire to follow similar foot steps.I have taken last 6 months to educate myself and currently own a single family home as primary residence and would like to expand to multi family properties (2-4 units) for additional stream of income, not to mention potential tax benefits for long-term investing.Based on current living situation, I have a fair amount of equity established in my primary residency along with having enough cash to either pay off house completely or use towards investing in a multi family property.Given that I'm the sole source of income for our household with my wife being the home maker for our two kids under 2, trying to weigh out risks with getting started now or perhaps waiting. 

Many insurance companies do not allow adding a landlord as additional insured.  

That is in addition to clauses that require anyone that stays more than 7 nights in 12-months to apply (then it becomes our choice if they are treated as a temporary occupant or tenant) and prohibition of subleasing.

Second, I'd connect with some local hosts in your area also in addition to Airdna.

Great use of space and provides additional income to offset the monthly payment.Orlando, and many other cities, have a "missing middle" problem in regards to housing. 

Additionally, have a clear budget, factoring in potential repair costs, and ensure you understand the rules about earnest money deposits and closing deadlines.LLC for Real Estate Investing: Forming an LLC for rental properties can offer liability protection and may provide tax advantages, though the tax benefits are non-existence for rentals.

Properties below this threshold present additional risks and more limited borrowing options.7.

If we sense there is a red flag, were asking them to upload additional documents like tax returns w2's etc.

Additionally, working in a small-town market taught us how to effectively price properties for faster sales without compromising profit.