I jumped on this and just finished my conversion of a 3 unit property in a hot area (Mission district.)

In the historic districts that you are talking about I think it's all about maximizing the properties that you have.

Most families would like to be settled in their home/rental/new school district prior to school starting.

If you work with a Realtor who is knowledgeable about the city, neighborhoods, school districts, etc, and will keep you up to date on the market for your investments, then the risk is minimal.

Bottom line is I have done this many times but stopped about 10 years ago when I moved to Carmel Valley with my daughters and stopped buying & moving so much so my daughters could stay in the same school district but now that my kids are older I am considering renting my home out for about $6,000 per month (payments are $2,500) and getting a 2-4 unit in a more urban area with an FHA loan.IF you have a chance to buy and can afford it i'd go for it.

To the east of SU is good for student and faculty housing, then the James street area on the north side is good for numbers but sometime spotty in neighborhoods.

I would consider myself lucky if I can find a SFH (3b/2bath) below 500k in a good school district.

My preference is finding properties here because very high ranked school districts drive demand in Dayton.- I can't speak too much about the north city of the city demand-wise.

What if you have kids in school and there aren’t any multi-unit properties in your district?

My home is located in the Stuy Heights historic district.