You might consider using accounting software tailored for real estate investors, which can help streamline the process and keep everything organized.

Software takes care of the rest. 

What software should I take advantage of that will help me analyze deals, comps, market research, etc. 

It is the mostpopular software in the industry and all CPAs know how to navigate it which isnice.

Tampa has a lot of draws, to name a few is Beach, Boating, Golf, Casino, Intl Airport/Biz Travel, Busch Gardens, NFL/NHL/MLB, Concerts/Festivals, and more.I would say Sarasota is a submarket of Tampa but has its own attributes as well. 

Rentler.com - seems to be a free listing software.

I'm planning to have a separate bank account/accounts for my entire portfolio, just wondering if anyone has recommendations for software to use as someone who'll have buy-and-hold and will be working with a property manager?

We have a collection process through our management software we use.5) small dollar amount in Iowa I'd say go for it yourself.

Listing the pros and cons of the softwares you currently use would be helpful, too. 

We do have a couple engineers in our program, but the majority come from all walks of life – home builders, software engineers, dentists, fix n flippers, home wholesalers, real estate agents, shop owners… to name a few.