Buying sub to also has risk especially if the property is being sold at an inflated price due to the sub to which is the case on properties that have not sold for an extended period of time.  

There are cheap options but they take more time and effort and are probably only worth it if something else is extending the timeline. 

Basically an informal audit of ones portfolio.This could be as simple as creating a few benchmarks (specific ratio of expenses, total PM fee ratios, vacancy rates and duration,etc)As much as one could assume they have a well oiled portfolio, an outside investor could find areas of improvement.

It easier for tenants to feign attempts at assistance, thereby extending the timeline for any necessary evictions which does ultimately impact my cash flow.

Duration, long-term, is usually where the benefits of investing come in.Everyone admires people that have done something successful that they're trying to do.

Ideally, I’d like to extend the property line to the house I live in over 2 feet (where the other house is currently standing).

You two could probably extend the closing until the repairs are complete which would be great for you since you would not have to go back on the market.

We either make sure the booking extends over the holiday, or just block a night out and then the cleaner comes the next day. 

High level $200k for a $36k gross return is a low yield..however I think there are a few variables..with 35% down you should be able to get stronger lending terms, if the seller is workable you could entertain a concession towards a rate buy down for lower obligations, possibility to look at shorter duration (ARM) loans if you only intend to own 3-5 years which could also offer a lower rate.

It will show up when a word you search for is in the listing description either in the Public and/or Extended remarks.