Buying investment condo

[Dan Cahill]

Is now a good time to buy condo's in Boston suburbs?

My mentor/broker is now advising I consider building a portfolio of condos, instead of CRE

It's still a hot housing market here, so one must act quickly when a listing pops up

Meanwhile cash earning 4.4% risk free in MM fund.  

This would be my first foray into real estate investing (I do own my own home as well).  I like this particular suburb (Natick), but am always fearful of buying assets when things are hot/bubbly.  I can generate income through MM fund/treasuries/dividend stocks/selling covered calls/cash secured puts, without ever leaving my home or having to deal with tenants.  I'm not adverse to putting in a little work owning RE, it's just I feel recession risk is very real right now, and there could be some great deals to be had in the not too distant future.  Any advice is appreciated.  

[Sean Kelly-Rand]

@Dan Cahill - back in 2010-2014 in Boston, when we were buying, condos were some of our most profitable investments because they traded at such a large discount per unit to the multi's because of the difficulty financing. Also when we resold as condos years later we were taxed on long-term capital gains as they were condos already (if you convert multi to condos its short-term cap gains).

Given the cost of ownership (including my own time) I won't buy unless it's a steep discount or I have a strategic reason (buying my own office space).  

In the meantime I've re-invested into our fund that lends to developers it's a good return relative to treasuries. Why buy when you can earn better returns at a lower basis?