I typically advise to buy as big of a home as you can.

Just for future advise if you have equity in your home its best to get a heloc ahead of time and just have that credit line open similar to a credit card so you can tap in to it whenever needed weather it be to pay off debt, or invest in your next property or for family emergency.

My better half actually advised me from the get-go to let it go (I have a t-shirt which says "Let that shitake go!").

I would advise you to approve this applicant unless there is a strong, objective reason not to - such as eviction history, a recent criminal conviction, or their income (including all disability income) is less than whatever standard you have used for all of your past tenants.  

I always advise home-buying clients to research home warranties (aka avoid them), and I wouldn't even consider it if it was an investment property.

A rule of thumb I use to advise my clients is: 1) the loan guarantee is worth 20-25% of the deal, 2) finding and vetting the deal is worth 25%, 3) executing the business plan for the property is worth 25% (i.e., overseeing contractors/property managers, etc.), and 4) contributing the money is worth 25-30%.

He is not a lender, his contract is for "business advising"2. 

I would not advise working with any PM unless they are able to provide all of the necessary reports for the property - Cash Flow, Income Statement, rent rolls, T12, etc.

For example, Florida checks all the boxes except insurance costs, which is why we advise our clients to shy away from Florida as it significantly impacts cashflow.   

I am also new to Real Estate and have been advised to start with a house hack.