However, I am unsure on how to go about finding the proper handyman/maintenance guy/management team to help run any out-of-state investments I make.

So I bought this fixer upper for 65k, had a low monthly mortgage, used the extra money to rehab out of pocket for the next three years.

I just completed my 20 hour course for my Illinois Mortgage Lending License and the final step is taking the state exam.

The president has zero impact on underwriting guidelines and  zero direct control of interest rates. in fact the fed has no direct control of long term rates that effect mortgage rates.

I'd like to use this to make an "all-cash" offer on a SFR, and then convert that to a conventional mortgage to pay off the HELOC.  

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

The rent from this property covers the mortgage.

I do not understand your remark as related to the DSCR loan.  2 ADUs are not allowed by f/f conventional financing but is not always enforced.Fortunately if you stay with the current tenant without a refi, by the time you pay principle it is likely the rent will have increased enough to absorb the increase mortgage payment. 

If you buy properties with little/no ability to drive value then you'll rely on appreciation and mortgage paydown to increase your equity.

I can assist with the real estate side of things - and probably the mortgage side too.