After a month or so of getting the house ready, I've fallen in love with improving the home and managing everything the property needs.This leads to the main purpose of this post.

It can be tough finding the right deals, especially if you're mainly searching on the MLS.

In any case, it really depends on what your main objectives are. 

We rent single family homes above median rents, fully remodeled and we don't use carpet on the main floor at all. 

If any one has experience with this it would help (Mainly the lending process) Toronto is a vibrant city with lots of renters but it’s also expensive and renters have more rights than landlords. 

We liked the TL home and nice lakefront view but here are some cons: pretty far/isolated, no real dining options outside and besides the music festivals/BNP tournament, didn't know if it would do well as a STR. 

I put Branson because that is what I am near, but I am interested in lots of areas, mainly Florida.Are rates really so bad right now that a first time STR buyer with 20% Down should not even try? 

I was looking at going the self-managing route due to me having a little more experience and mainly finding a great handy-man and GC in the area to help me if repairs were to come up from the tenant.

Personally, I would recommend purchasing the primary residence first, mainly because of how the DTI is calculated.Scenario 1: If you were to purchase the STR first, and then the primary residence, you will likely need to qualify with the full payments on both properties depending on your timeline.

For example you can build an ADU to rent out as an STR and stay in your main house, since this is still your primary residence it seems that would be an allowable use.