we have two properties under agreement and both are $2M + and VA loans, which i was shocked they go that high, so yeah they are powerful.

Agreed with @Robert Ellis here - Can't go wrong with a Triplex!

So if my taxes and insurance numbers are similar from house to house, then the low-rent houses are not going to have enough revenue to take on more than just a little debt. 

If you sell your only overachiever to go with a more leveraged position, you could have 2-3 properties that may cover themselves or even provide a little profit, but when the rental markets shift (and they do), now you have 2-3 properties that all require you to supplement for their shortages. 

Personally a big pass for me going forward on funding.

Make sure the buyer will go through with the sale before you worry about the timing.

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whats the issue if you are the one underwriting the loan and it goes bad it should be quite rare to now want to charge your investors for something they did not do I suspect is going to be stepping over dollars to collect pennies.. taking care of your clients long term is part of doing bizz like Chris mentioned.. 

Realtors, supposedly the experts) think is a going value at this point in time.