Try EBay for bikes and clothes. Also Craigslist.com. Also look at local pawn shops, police auctions, and Goodwill/Salvation Army stores.
As for him leaving you in the dust: maybe you can work out a route where you both leave together, he can take off and do his speedo ride and you ride your pace and the 2 of you meet back up towards the end. I know several women here do that with their SOs.
As for the best bike for a newbie: bikes are like shoes! You need to just go try them out and pick which one fits you the best, then see if you can find a used one. You may also find a road bike too squirrely or too hard to ride due the bent position. So test riding would give you an idea what style of bike you're looking for.