Should we buy a single family in very expensive towns in MA?

[Connie H.]

Hi there,

I posted here as a new member 8 month ago. Basically, we finally sold our negative cash-flow condo in south MA and at least got our loss stopped. We plan to buy a single family in a very expensive town - Wellesley in MA and sell our current residence.

My question seems dumb - should we risk to buy a 1.5-1.7M newer SF and to be bound to the mortgage forever and work our whole life to pay for it, or should we buy a SF around 1.3-1.4M which has much worse condition comparing with the above? While we could potentially save to get a multi-family for investment much sooner with the option 2?

With the first choice, we will have a 1.1M mortgage, and work very hard to pay for it. About $9000/month. If one of us loses job, we will be under a lot of pressure and even may need to sell it - or we need to sell our only investment property a multifamily in Boston to save it. Of course, you can say that WHY you need to buy it? You can live comfortably in other towns with a much less expanse on primary residence and focus on investing...That is also what we have been asking ourselves for a while. The first reason is for the public school district. The second is commute. The third is for investment purpose. Properties in Wellesley and Weston are roaring high in the past decade and sometimes makes more returns than a multi-family, and it is easier to keep its value when there is financial down-turning.

I understand that it is totally a personal choice based on the financial situation of a family, personal preference, and personal understanding and sense of risks/benefits with regarding to such choices. It is like walking in the fog and not sure what is the correct option.

Thanks so much for your input.