First time home buyer house hacker

[Alfredo Sanchez]

I'm looking into buying a property with a sibling and renting out a portion of the house to help with the mortgage. We're approved and have been outbid several times on homes where we offered 15-20k over asking. 20K over asking on homes that needed bathroom and kitchen remodeling as well as other minor touches. Supposedly most of the houses we looked at always had 10+ offers so we took some time off from looking at homes in order to not compete with families who were looking into moving into a home before the new school year. 

My sibling and I aren't in any rush to buy a home but we're hoping to make a move soon and give it another shot in acquiring our first home. The question here is, should we wait for the market to calm down? Or pay top dollar leaving little room for future appreciation gains? 

Another option on the table is buying a short term rental property in the Poconos, PA on my own. The goal would be to generate equity in that home to than use in the future to buy a home on Long Island when the market is right??

Any other strategies I should look into?