Personally Sept 1st and Oct 1st are the same in my market.

I grew up in Cleveland and personally own a S8 rental.

I figured i needed a "company" to have my commissions written to, instead of me personally. 

Personally, I like to essentially do a move in inspection.

It requires the right person and some good mentoring, training and oversight.   

My personal home almost doubled in value in 2 years and while many markets have gone down the last 6 months, we've been mostly flat.  

If the new builds are larger and you do not need to do any work, that would be the option I'd choose personally. 

You could do that for 3-5% down.. live in it for a year to meet typical requirements for use… then move into a new house, and ‘voila’ - you bought your second (multi-family) rental for 3-5% down instead of 20-25%.It is entirely possible though that you will face debt to income issues on your first rental if your lender wants to see a year or twos worth of rental history before counting your rental income to offset your debt payments…so beware of that.Otherwise you may have to look at creative financing… maybe bringing in a money person where it was a short term investment for them, like “I’ll give you 8% on your money (versus the 4-5,% you could earn from the bank CD) if you will partner with me on this purchase.”

Was this property ever rented or just always used for personal use?

This again puts another $6-$20k in my clients’ pockets and getting a more personalized and boutique experience rather than being just another number.