rent out or sell; buy or rent?

[Gubmentdoc]

Looking for advice with my current situation.  I'm moving from lower cost area to higher cost area ($150sq/ft->$300+/sqft).  I'd take away about 200K if I sell my house (bought for 565, worth 740 now).  It has carriage house which we've been renting for about $1500/month and could rent out main house for about 2800/month...current mortgage 3000/month.  Reasonable quality 3-4bdrm homes are in 800K range in new location but similar rentals are about what I'm paying for my mortgage now.  I have 50K in savings account,  my current loan is VA loan but I could get another 161K from VA loan if I keep my house and I'd have to come up with 25% of the delta for down payment if I bought (I'm 100K short on 800K home purchase) unless I used doc loan.

1. sell current house or rent out keep equity tied up and ~1000k/month cash flow?

2. if sell house, take 200k and put towards down payment on new house or invest that money and rent in new location?

[antheus]

if you rent the house you bring in 4300 a month. Less 3000 mortgage, less property taxes (500 a month?), less maintenance, factor in costs of finding renters and cost of being unoccupied and your home is suddenly cash flowing much less than 1k a month, maybe more like 500. It has already appreciated 200k, you've won the game. I'm not sure how much you earn but in all likelihood it's enough to make the cash flow not worth the time/hassle.

[StarTrekDoc]

If you cash out now; tax free.  If not, time clock starts on five years.

Also, rental market of that house + granny flat has to be determined and local manager if you're away eats into costs and headache.

Also, do you really know the new job in the HCOL?  rental there for the first year and carry the first home still would be advisable as to a return landing spot if all doesn't do well at the new digs.   This is the benefit of the 2 of 5 years gains rule.

Don't be so hurry to sell OR buy.