Here’s a summary based on the responses:Tax Rates and Holding Period:For flips (properties bought, rehabbed, and sold quickly), profits are taxed as ordinary income, not capital gains.The holding period is calculated from the purchase date to the sale date.1031 Exchange:1031 exchanges apply only to properties held for investment, not quick flips.If intending to use a 1031 exchange, I must reinvest the proceeds into a like-kind property within 180 days.Holding a property for less than a year may disqualify it from 1031 eligibility due to lack of demonstrated investment intent.Thanks again for all the helpful advice!

This had to do with lack of communication between Lender and borrower.

I lacked the architectural knowledge to design my own.

It lacks a little in the property accounting side though, so if you end up growing your portfolio, it might be more useful to use software with additional features such as bank feed integration, advanced tax reporting, and receipt scanning. 

Plenty of people out there have the money for deals, but the lack the time and energy to FIND them.

For me personally I like mid-sized/regional bank as you are not just a number like with a national bank, but they still have some of the bells and whistles like good online tools that small banks lack.

However, I know this will be very difficult to pull off and is a high risk, especially since I'm already using a lot of time for my full time job and building up my insurance agency on the side after work.

You can read up on "Disparate Impact" Theory on a variety of landlord resource websites, including government agencies. 

Their paper assets, on their paper accounting, can't pay the bills because they lack the paper to pay them. 

Be more polished, informed, and hard-working than your competition.One of the biggest complaints I've heard regarding RE professionals is lack of responsiveness.