Purchase price: $380,000 Cash invested: $19,648 Sale price: $485,000 Not really a portfolio investment as it currently my personal residence, but I'd still consider it an investment.

I want to buy a studentroom (very popular here, cash flow each month around 400) for about 80-90k.

I normally end up going with a small bank that provides favorable terms for holding my cash.

The listing shows that it has the potential to cash flow around 5K per month after paying for the loan.

I bought it last year because I thought the price was pretty good considering it's located in Brookline and gives good cash flow.

Purchase price: $726,000 Cash invested: $1,300,000 Sale price: $4,500,000 We are developing a 4 story a luxury Duplex.Property is primed for short term rentals with conservative estimates of ($40,000-$50,000) per month.

I would say sell - every day of the week from a cash-flow perspective.  

There are a lot of pros about the property including that it would be cash flowing approx. $600 per month if I were to move out.I guess my question is how do you know when to take risk and when not to?

We currently own one door (split acquisition and closing costs and contribute equally to management and ownership), and have split equity and cash flows from the property - also pretty standard in my experience.My question is this - I want to purchase a house hack and would like to use our current business entity for accounting purposes (tracking income / expenses / etc).

@Brenda FreemanI think seller finance can make sense when you can get an at or above market price; you don't need the proceeds; you want the monthly income; and delaying the proceeds will make sense from a tax perspective.If you are saying there's an existing mortgage you would have to pay off yourself, then I don't think that makes any sense - why would you want to invest your own cash to make this work?