Besides the lender agreements, you will want to consider the income tax implications. 

End of tax year?

I wanting to make a career change and was curious if it makes sense to do all , if not majority of the renovations and pay myself instead of paying contractors?

This are the numbers:25 unitsAsking price 1.5MI will offer 1M $11,780 monthly rent income$13,000 annual expenseYes, the expense ratio is low but it's because it's in the island where we do not have property tax, insurance is for liability around 2k a year and it's all concrete structures. 

I recommend having a plan to pay down the heloc within a relatively short time frame (1-2 years) as it's a revolver and is not meant for long term financing.

If I went to the investor and said "hey, I'll pay you $x amount per month to keep living here with the intention of buying it later" would that be an attractive offer?

For example, if your lease does not make any other charges to the tenant "payable as rent" or "payable before rent", then you might not be able to evict if they don't pay these utility bills to you.

You can raise capital to pay for your down payment and it is by doing a syndication or private fund.

I am surprised that my lender is asking me to access Social Security Records and a tax transcript.

You can also pay flat fees if you think an agent would add value.