While I do feel I am overpaying based on the arv value of the properties, I am comfortable with the price due to the owner finance and positive cash flow that the property generates.

If you're able to position create an ADU the fees should be much less.

Canton happens to be my favorite neighborhood due to its close proximity to 95, major shopping outlets, the water, and overall positive vibe of the Community.

I would be also looking into reinvesting the earned cash flow therefore continuing to make business if I have a positive relationship with them. 

I think I may have seen that property, unfortunately we weren't 100% positive we were ready to buy again until now.

I ran my numbers pretty conservatively and still see a $350+ per month positive cashflow.

With mortgage interest rates at 5% they are losing $433/month or, to relate to cash flow, they are eating $433 of their positive cash flow before they deduct any other expenses.

Show us the numbers and you will get all the feed back you need to make a decision.Keep in mind SFHs are notoriously poor at producing positive cash flow.

Then, once each rental is done this way and applied to income or debt, they are going calculate your DTI and qualify or deny you based on the DTI requirements of that particular loan program (28%, 30%, 35%, 40%, 60+% back in 2005, whatever).The above underwriting method is know as "washing" the debt of each rental property with its income.Another way that they do it is they simply take the PITI of each property straight to the debt, and the rental income from each property straight to the income (usually also reduced to 75%); rather than washing it first.It is advantageous to the borrower's qualifications to "wash" the PITI with the rental income and then apply the remainder, whether positive or negative, to income or debt. 

Of which both sides will be renovated and ready for tenants in the next few months.We're ready for our next property and would like to do one more hack before buying pure investment from the onset.I don't want to kill our cash cow, but I can't ignore the fact that selling at a peak could put us in a position to grow our cash cow heard.What are your thoughts?