If you could configure the bedrooms to be able to sleep 8-10+ people, your ADR could increase even further from there.However, if you go the STR route, make sure you factor in the time commitment it will take to manage the property. 

Factor in an eviction cost and expectation if needed when you are looking at numbers. 

You can't go off of the cost estimate on permits and even beyond that, design, site work and a number of other factors will play a significant role in costs.

Raising the rent depends on multiple factors but most of all is market trends.

Your taxable income may be more than $150,000 since you have to factor in depreciation.You can potentially consider doing a 1031 exchange.

How long it takes to rent depends on a lot of factors.  

It can be a negative factor if there's increased traffic/noise or if it blocks off a view. 

Will depend on several factors like the type of property, type of tenants, your risk tolerance, other assets you own, your estate planning, laws where the property is located, etc.

It could be an easy fix like this or a bigger problem depending on the factors at play (are the joists accessible, will it mess anything else up if you just jack it up and reinforce, is there water damage or structural damage to the foundation causing the sag instead of just old joists, anything else going on like a supporting wall or posts under the floor, wiring or plumbing runs involved etc.).

All it's looking for at that point is total liquidity, credit score, factors on the property itself.1040's, pay stubs, Debt to Income ratios and things like that aren't a factor here.