I'm currently beginning work on a descendant of Uatakassí.

There will be at least a couple of millennia separating it from
Classical Uatakassí.  Some ideas I've come up with:

Geminate voiced stops become nasal-stop sequences (i.e., bb -> mb, dd ->
nd, gg -> ng)
/g/ is lost, I'm not yet sure exactly what it becomes.  Two
    /g/ -> /N/ (inspired by Japanese's use of [N] as an allophone of
    /g/ -> /G/ (and perhaps then -> /x/ -> /h/ -> 0)
/C/ merges with /S/
Possible deaffrication
Geminate /l/ becomes lateral fricative
/zl/ ([zr]) becomes /r/ (alveolar approximate)
/sl/ ([sr_0]) becomes /r_0/
/fl/ ([fl_0]) becomes /l_0/ (perhaps later voiceless lat. fricative)
/vl/ becomes /l/
Possibly /lw/ -> /l~/ (velarized l)
Possibly /lj/ -> /L/ (palatal l)
Possibly /kw/ and /gw/ -> /p/ and /b/
/v/ and /w/ merge, with [w] used adjacent to consonants (perhaps also
word-finally), and [v] elsewhere
Long vowels become short when in closed syllables
/au/ and /ai/ become /o:/ and /e:/
/i/ and /u/ split, /i/ becoming /i/ and /e/, and /u/ becoming /u/ and
Possible development of tones
Possible loss of phonemic length in vowels (perhaps replaced by a
quantitative distinction)
Possible loss of phonemic gemination in consonants
Possible simplification of CL clusters
Possible /f/ -> /P/ -> /h/ development

Becomes V2, by the frequent use of fronted topics, which eventually
became mandatory; perhaps retaining verb-initial order in subordinate
Loss of the Classic tenses, the past tense replaced by the perfect
aspect, and the future by the prospective aspect.
Most of the aspects will be replaced by auxiliary verbs.
Might become accusative
Most of the verbal prefixes will be lost, replaced by auxiliaries and
Loss of most of the cases
Consequentially, greater use of prepositions, and development of new
Simplification of, or possibly complete loss of, gender system.
Most likely, simplification into three genders, "sentient" (from
classical Gender 1, "sentient female"), "animate" (from classical Gender
5, "animals not associated with people"), and "inanimate" (from
classical Gender 7, "inanimate")
Development of a definite article, from Classical Uatakassí _fúnu_
"that, previously mentioned"
Loss or reduction of incorporation
Reduction of many verbs to suffixes (mostly verbs that frequently
incorporated objects)
Loss of many Classical verbs to be replaced by noun-verb compounds (a
phenomenon which had already begun in Uatakassí, replacing, for
instance, "inspire" with "give inspiration"), thus the relexes of glí
"make" and labí "give", the most commonly used verbs in those compounds,
will become common verb endings
Simplification of variable stems

Cenedl heb iaith, cenedl heb galon
A nation without a language is a nation without a heart - Welsh proverb
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