The consideration for the property to cashflow (after you move out) is still very important if you plan to hold, but taking action with the consideration of how this first step will impact your finances today will yield the greatest impact. 

Picture it like a dart board—areas farther from the center experience increasing pressure, leading to appreciation if you plan to cherry pick any to hold onto.

I’m Cheyenne, my husband and I are just starting out on this real estate journey in the Detroit area and the plan is to begin with single family fix and flip (or use the BRRRR method starting with single family homes).

A cost segregation study is a strategic tax planning tool that separates the assets that have a shorter useful life and can be depreciated over 5, 7 and 15 years from the residential rental property or nonresidential real property that are depreciated over 27.5 and 39 years, respectively.

@Spencer Cuello As others mentioned, can be used if it's short term only and you have a plan to pay off before the 0% expires.Also note it's best used for the rehab portion of a deal after the purchase is complete. 

I plan to invest in a property in Florida worth no more than $1.5 million.

Send him a letter, emphasize that you are personally yourself the end-buyer, include proof of funds, include something attesting to you being financeable (unless your proof of funds is for the full cash purchase price).If he owns 20 local businesses, good chance he's in at least one chamber of commerce, and if he's not, he 100% knows people that are, who will spill the beans and offer to do an intro if you mention you're interested in buying a gas station over a beer or a meal (there's probably like 3 people in that city that fit this description, why not get introduced to all 3?)

I give this plan a 1% of success.

There are plenty of quality Communities out there, you just need to find one (or several) that has a culture that fits your personality.The other thing you could do is become accredited through taking the Series 65 exam. 

My plan would be to actively manage the new property and hire a property management company to manage the first property.