Being the optimistic person that I am, I would want to get both businesses. But I would want the best one first. How I would do it is get all the way from where you are to LOI to close on the first one. Stay involved with diligencing the other one. That's what you should be doing anyway. Just before you close on the first one, make an offer at your preferred price and terms for the second one, set to start exactly 365 days away. Use a $1000 deposit that you have to be willing to lose if things don't go well. But if things go well with the first one, then you have the first step in expansion. This strategy balances what for me is optimism with being pragmatic. Hopefully also by that time, you and the seller have a decent working relationship, and you've essentially offered a stalking horse bid (I think that's what I've seen it called publicly) for the seller that maybe may cause him to have second thoughts about other offers that he gets in the interim year. It also depends on you succesfully taking over and starting to grow the first business.

1) Do not buy both at the same time. At least 3 months apart. Learn culture, employees, customers, of A before picking up B. 2) Throw integration out the window for at least a year. Happy to share examples.