The current property has a VA loan with a pretty great interest rate (2.375%). 

I am having trouble figuring out whether to go with a hard money lender, or a conventional loan for my first rental property.

The purchase decision only requires online thorough research, then try to buy in a 401k/ira so you don't have to pay taxes on the Dividends which can be large.

I've been searching online for trying to find a loan servicing company that provides the services in Florida.

I have one myself that I funded after selling my SF home and once I set up my policy, I took a low, simple interest (5.5% for me) loan that I then used to purchase a 4 unit MF; now I'm using it to fund the renovations.

I had planned to open both custodial accounts and Roth IRA for them, then pay them through online payment from our business account to their custodial accounts, then transfer the money into their Roth IRA accounts.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Most realtors can not get much loan due to nature of his un-predicable income as 1099 and have terrible credit score issues.

I’m getting stumped on how to get a loan that works.

It still wouldn't be enough profit to do this full time without another job.I see lots of people online who have quit their full time job and are doing Real Estate Investing only, buying new cars, being able to travel and I am wondering if this is just their "online persona", it is because of the amount of properties they have that has given them this financial/work free freedom or I need to find somewhere else that would give me a larger return.Either way I am still moving forward on my journey :) I was just curious because that would be my dream goal to not have a 9-5 and my investments give me that freedom.