This will accelerate your plans and you will meet those people organically instead of awkwardly calling up randos and trying to vet them that way.One of your four might lead to the other three.Check out meetup.com and the Bigger Pockets Events section.

Space was awkward and I had to re-arrange the layout.

It’ll be awkward and you won’t know a ton but it’s a great place to start and Brand Krieg is a great facilitator. 

That was awkward) but at my CA property people arriving/leaving early/late happens ALL.

Would the awkwardness you described drive you away at first sight or effect your needs as a renter?

Sometimes if you have an awkward space that stays empty and rest are full the landlords will put a weaker tenant in there.

Most of the buyers agents fears with FSBO is that they're going to get shortchanged their commission or that they'll have to have that awkward conversation with their buyers that their services aren't actually "FREE" and that their clients are going to need to pay them at closing... depending on their beginning sales pitch / buyer consultation that can be a very uncomfortable conversation.   

I have looked at a few others, some of which are really awkward.

The tenant may be testing you to see what they can get away with, and it is far better to start out on solid footing, as opposed to letting things get awkward because the tenant is trying to take advantage of you.

When looking at investment properties, sometimes I come across ones that have tenant at will, usually long term tenants who are paying way below market rent.How do you guys handle these situations to try to bring the rent up to market value in the least awkward/ painful way?