>I'm seeing my best value in booking flights....i'm considering spending money on airbnbs instead of booking hotels thru points...
This is most often the case - flights can be great value but hotels often not as good. On our last 2 visits to Italy, we did all Airbnbs except 1 night in a hotel when we just needed a place near the Milan train station. Italy has some great value Airbnbs.
Amex doesn't have great options for hotels or cars when booking directly (0.7cpp as you say) so these are best used for transfers to hotel or airline programs. afair my last Amex bonus I transferred all the points to Delta. As a hotel option, Marriott has a ton of great hotels in Italy and you can get the 5th night free for a 25% increase in point value, as long as total valuation works out and you plan to be in 1 city for 5 days.
For UR points, you will get at least 1.25cpp booking hotels or cars via the Chase portal, or with the CSR 1.5cpp. There is no reason to get 1cpp booking hotels - you would be better off booking the hotel directly with the Chase card (2-3pts/$) and then getting a statement credit. Or booking via hotels.com and getting 10% back for future stay plus Ebates/Rakuten cash back (outlined here:
https://www.gocurrycracker.com/maximum-hotel-value/)
A point of caution: Selling miles or points is a violation of most terms and conditions, with risk of having your account closed and all points forfeit, so be sure you accept the risks before going that route. For people you know personally, e.g. friends and family, you can book flights through your own account and accept some cash.
