I assume I need a CFP first to figure out the Roth conversion part and once converted then in comes CPA? 

As I've been learning, there are the key taxes to understand when investing into a new area or state:- State business income tax (if you have an LLC)- State personal income tax (if they want to tax you too, even as an out-of-state investor)- City personal or business income taxes- Any registration fees due the city/state- City/state property taxesAnd I'm sure more!

I have found it difficult to find financing being 22 with my only income being from house flipping.

I do not have any 1 BR STRs/MTRs but I have seen annual STR rents based on bedroom count in both my market (San Diego) and emerald coast (one of the markets I have made offers) and the difference in the income is substantial between 2 BR and 1 BR.  

I've always used my business solely to generate an income/paycheck, however I'm ready to transition and use my experience to facilitate investment opportunities.

Depending how much you earn you can step up those savings by getting a side-hustle.

You will need to work with a tax professional to analyze your current tax situation (income, deductions, activities, etc.) as well as projected income from the fix and flip business.The benefits have to outweigh the costs (payroll costs, additional tax returns, more stringent reporting and compliance requirements, etc.).One important note - an S Corp is not an entity; it is a tax election.

Bear in mind I'd still work, say a few days a week and make enough income between rental cash flow and working to clear my annual expenses by at least $25K after taxes.

@Jeff RyersThere is a basic rule of thumb for income qualification but I use an additional one as well. 1.

It seems like at this moment you need active income.Real estate can generate income for you but it takes time.