We've lived in it for 3 years now, (have a 3 year old) and now I'm questioning my original strategy due to development in the area and because its appreciated fairly substantially while we've lived in it.

This is basically what it is all about plus tons of marketing.ExampleHave the local seasoned wholesaler in your target market amylose where you will be marketing.

Have you developed a follow-up system?

So the returns have to be much more than just a little better then existing buildings for turn around's.You need to get with not a guru but a local multifamily to regional developer for lunch.

I feel stuck.The "best" bid so far for lawn care is $1750 for the 5 month season.  

If not, a lot of lenders are going to require that $150k to sit & season in your account for a few months.

Exception:  you are an employee of the owner (typically builder/developer) and showing only their properties.That being said, I know of lots of people that are doing just what you propose, and are doing so knowingly or unknowingly breaking the DORE laws, at lest for NY and PA. 

We finally just developed an in-house system for our own use that has worked out great and given us a marketing list that no one else has (or only a few people).   

A creative option may be buy the 4plex first and develop a relationship and purchase the other parcel later once every goes well, but then I would need to refi with traditional loan to have all 6 under 1 loan at the 5/10 year option.

@Clint Harris If you are willing to go with a commercial loan, you should be able to lessen the seasoning period required or avoid it all together.