Sorry for the sarcasm, but if you’re asking for investment advice on an internet message board, you’re asking for it! As for purchasing real estate, I have nothing against it. Some of us here have already gotten incredible deals that would have seemed impossible only a couple of years ago. There are lots more of these deals to come. Having owned (and sold) a condo in Hillcrest and also having talked to many condo owners here in SD, I can give you a few pieces of advice (with no sarcasm even!)
There are good buildings and bad buildings. Good buildings have a large percentage of owner-occupied units, good participation by homeowners in the HOA, and a healthy surplus in the HOA’s bank account. When disputes arise between homeowners or when there are problems in the common area (as there always are), the homeowners roll up their sleeves and get things taken care of. In these buildings most of the homeowners know each other and while they may not be friends they are cordial to one another because they understand that they all share a common interest. They spend their HOA money wisely and (most importantly) they pay their HOA dues.
In good buildings, renting out your unit (especially to short-term vacationers) is likely to be frowned on at a minimum and is more likely to get you in big trouble with your HOA. Most good buildings will not allow short-term rentals.
That said, if you really want to buy a condo and rent it out you will probably not be able to do this in a good building, so you’ll have to settle for a bad one. What’s a bad building? It has a large number of “investor” owners that rent their units out, who never come to HOA meetings, who never vote for HOA increases even when the HOA bank account is empty and the common areas are a mess, who simply don’t pay their HOA dues requiring the HOA to spend money on attorneys, etc… Such buildings can be nightmares to live in, especially for those foolish enough to purchase an owner-occupied unit. Your neighbors are likely to be young people having lots of parties, or vacationers tracking sand down the hallways and parking in the wrong spots in the parking garage, etc… It can be difficult to sell a unit in a bad building, especially when there are lots of units available (like right now).
There are not a lot of good buildings and units in good buildings command a premium. Do your research carefully before putting any of your money in a downtown condo. There are nice units available but the prices could still come down. I know of one or two good buildings but I’m not going to name them here because that would be giving you the benefit of my work and research without you having to do it yourself 🙂 They won’t be hard to find if you look carefully.
The newer buildings are the biggest risk in my opinion as their HOAs have not been operating for very long, and they are likely to have many “investor” owners that expect to be able to just throw a little cash down and then have their “investment” magically maintain or increase its value over time without them having to do any work. Many of the newer buildings still have lots of vacant units which means that the HOA will be in big trouble from day one. Also, most newer buildings have ridiculously low HOA fees (to entice buyers) — it is not uncommon for an HOA in a new building to be flat broke in the first few months after everyone has moved in, requiring an increase in fees. This is true even when the HOA seems “high” like $400/month. It is not cheap to pay for swimming pools, 300 hallway lights and common area insurance on a $30M building.
