[Zunow]

Hi,

This my first post here, but I've been lurking up for a while. I've saved up a lot of questions, so I thought I'd give everyone a snapshot of where I'm at and then get to my questions.

Me:
- I'm 34 and recently sold a small business I started several years ago. I'm already working on two other ventures.
- Recently married, no kids (currently).
- I probably spend more money than I should (waste money on some stupid/fun things), and "only" save $1k a month.

Assets:
- $25k in IRA (startup has always had poor employee benefits/savings programs)
- $55k in mutual funds (from my regular savings)
- $625k in money market (from recent sale, not sure where to put it)

Income:
- I've started another company, raised a small amount of outside capital, and currently pay myself $10k/month; the business is interesting, but extremely unknown right now. I think we'll do well, but I could also lose my job in 3 months and I wouldn't be that surprised.

Debts:
- $525k on mortgage. I bought my San Jose condo in 2004 for $700k (doh!); it's probably worth $550k now.
- I will owe about $150k of taxes in 2009 (due to business sale this year).
- I've never had a car payment or cc debt or anything like that.

Wants:
- I'd like to put $50k into one of the new companies I've started. Again, this hope/prospects are high, but it too could also totally blow up. So after taxes and this investment, I'll have about $400k "extra" to invest somewhere...
- My wife and I would like to move into a house ASAP (from our condo).

My Questions/Ideas:
- How should I "time" the market to invest the $600k I currently have into something better than a money market at ~3%? If I would have initially moved this into the same mutual fund(s) my "regular savings" is in, I would have lost about $40k over the last couple months (glad I didn't!). Now I'm paranoid to do anything with it.

- Some of the extremely wealthy people that were investors in my original company have recommended me to a "wealth manager" (or something). I feel like I don't need this and don't have enough money for this today... Thoughts? Anyone here use someone like that? This firm charges 1.25%/year of your investable assets.

- My wife and I are thinking about (a) renting out our condo at a loss (probably lose $1k/mo), (b) buying a house we'd rather live in (have big dogs now) (it's a good time to buy), and (c) waiting for the housing market to recover (2-3 years?) and selling the condo then. The new house would likely be between $500k and $750k. 20% down on $750k = $150k + $3k/mo. Bad idea? Too ambitious? (i.e. buy 2nd now and sell 1st later).

I'd appreciate any tips or insight you may have!