It is rather difficult to make BRRRRs pencil out right now, so you should budget to leave some capital in the deal on the refinance. 

If you need to obtain it, how difficult will that process be?  

Add the difficult exit and your investor pool is very limited. 

@Khaled El Dorry This strategy is know as a consolidation exchange, and like what @Adam Bartomeo said a single buyer might be difficult to find.

In terms of STR it seems that in the really strong markets (Lisbon, Porto, old town Ericeira) it is difficult to get the AL licencing.

The test were very difficult and challenging. 

Were waiting to see how things are by the end of July here in CA (heros act ect) to see if we can serve her then, but even so, I imagine it will be difficult but I will mention this time him and see if theres hope lol.

If the tenants are the issue, they can make it very difficult to show the property and this can create a lot of issues for you during this time.It will also prevent you from selling your home for maximum market value as only few people will want to deal with holdover tenants.

Changing careers can certainly be a challenge, but it sounds like you're equipped with a solid foundation thanks to your sister's support.

Duplexes are cheaper to rent and expenses are becoming difficult for the average tenant.