For the $500 in old collections, I would first try a pay-for-delete (PFD) with those accounts... as paying off negatives from a long time ago actually makes them look fresh, with a recent date of last activity... and can actually lower your scores by paying them off. Doing a PFD will remove them if you pay them. You first need to ask the creditor/collection agency if they'll agree to a PFD. From my experience, rehabbing a student loan should definitely remove the late marks in the past once the rehab is complete... so I think you are being told correct information.
Self-employment does present a higher risk than being employed, however it wouldn't be the basis for you needing a sub-prime loan. Self-employed applicants qualify for FHA just as often as employed applications. Now is the income you are listing after expenses are taken into consideration? Since you said you are "profiting" and didn't use the word "grossing", I assume it is after expenses are calculated. If so, then your debt to income ratio would look great for FHA. I'd say you should try the PFD's, pay off the Cap 1's (assuming those aren't charge-offs/collections) to reduce your utilization, complete the student loan rehab... and you'll be looking pretty good. If the student loan isn't federal, and if you've been on the rehab plan for 12 months, then you might not even need to wait for that to be completed before you'd be able to qualify.
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