My current flip had what I considered ugly grey siding and I was going to replace it but decided instead to stucco the foundation, chimney, and used accent colors that played well with the grey, it looks great and I saved a load of cash by not replacing the siding.

Yes, the cost of its bookkeeping could be paid from the IRA; however, not if you use quickbooks for another business.Its like playing with fire.

It didn't prevent me from qualifying, but after playing with the numbers for a bit you realize even if you keep acquiring rentals that cash flow, your DTI will keep increasing, eventually pushing you over the acceptable limit.

The market was overpriced during the tail end of that period (right before the bubble), musical chairs were played by buyers who didn't know any better, and many folks got left out when the music stopped.

You might be able to get in the front of the line but even if you do get someone one the hook, it's still pretty risky.Keep in mind that most contractors are notorious for starting many projects at once and keeping them all in play so they will have a guaranteed workflow for many months.

There is an inability to absorb the increase in some areas so I am wondering how it will play out.

You contract from a seller, then sell to another buyer at an increased price, thus playing the middleman.

Her strategy is to pay down our first property considerably before buying another one, and my strategy is to buy as many as possible and use our current income to leverage more properties.We have a combined gross income of 250K and FICO scores north of 700 and are looking at properties in the 200-350K range in MA.I am not clear on the debt to income ratio and the role rental income plays in acquiring more properties.With the above figures (and provided my and my wife's risk tolerance reaches a middle ground), are there challenges with us acquiring multiple properties/year with conventional financing?

You just have to accept and know the rules of the game you are playing.

I've played the credit card game in the past.