To complicate it a bit more, I’ll add that we were also contemplating doing a flip as our first deal, then switched to the house hack idea, and now are going back and forth on which might be better to start.

At that point I'd consider myself financially free and would contemplate retiring from the 9-5 lifestyle. 

I'm also contemplating on adding my area (Calgary) to my company name, although this makes it quite lengthy and could be hard to search up for a potential seller.

I'm also contemplating on adding my area (Calgary) to my company name, although this makes it quite lengthy and could be hard to search up for a potential seller.

We’ve contemplated hard money but also wanted to consider Wholesaling a few properties to build capital.

The management agreement could also authorize the LLC to deal with the property manager and undertake other services that it seems you are contemplating for the LLC to handle.

However, this is a discussion for another thread and I won't say any more.I will enjoy my wine and hack on my acoustic while further contemplating.

I'm contemplating doing a 1031 exchange on an SFR and using the proceeds to buy a vacation condo that I will do STR's on for at least 3/4 of the year.

Is there a way to circumvent the employment history in order to obtain conventional financing (besides getting a co-signer), or should I start contemplating alternative ways to finance my investment?

@Jessenia Munoz Thank you for the post, this is the same sort of question I have been contemplating for quite a while now.