Thank you for sharing your story, and keep in mind, people with the same interests and excitement that you have about any subject shouldn't care what your sexual orientation is, and if they do, they probably aren't someone you want to do business with.

We are fortunate enough to invest in an area of Chicago that we can attract good tenants who are not high maintenance and who have so far not trashed our properties.  

As such, we've been successful so far with these properties as a result of our underwriting/modeling and also our property focus (areas close to public transportation, attractive to young professionals, bordering areas that have already "gentrified", decent relative cash-on-cash returns). 

I'm honestly more concerned for her, as she is an attractive 23 year old....I'm sure nothing would happen but if it did i couldn't forgive myself.

That was attractive to the seller and helped get my offer accepted despite 9 total offers on the property (it was listed well under market).

I prefer rental properties over flipping but I understand the attraction of raising capital by flipping.

Then center the meetup around providing value and attracting the type of people that will help you accomplish your why. 

Something she has is attracting them. 

Another twist will be to have a mix of long term rentals away from the tourist attractions and vacation rentals close to the beaches.I am looking for advise, tools, samples, insights on how to best create a business plan and identify the best tools (software/apps) for the establishment of this new company.

Whenever a state or a muni is willing to give away massive tax breaks to attract big, anti-union businesses, and in turn ask the citizens to pay little state income tax, it's clearly a "pro-growth" environment.